Transformation of carboxylic acid salts to aldehydes by stepwise reduction with borane and oxidation with pyridinium chlorochromate

Bulletin of the Korean Chemical Society

Volumn 22, Issue 10, 2001, Pages 1089-1092

  Cha, Jin Soon ^a   Park, Jae Hyung ^a   Moon, Suk Joung ^a  

^a Yeungnam University   (South Korea)

Author keywords

Aldehyde synthesis; Borane reduction; Conversion of carboxlic acid salts to aldehydes; PCC oxidation; Stepwise reduction oxidation

Indexed keywords

ALDEHYDE DERIVATIVE; BORANE DERIVATIVE; CARBOXYLIC ACID; DIMETHYL SULFATE; LITHIUM; PYRIDINIUM CHLOROCHROMATE; PYRIDINIUM DERIVATIVE; SODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0035540439     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (72)

1. (a) Brown, H. C.; Cha, J. S.; Nazer, B.; Yoon, N. M. J. Am. Chem. Soc. 1984, 106, 8001.
2. (b) Brown, H. C.; Cha, J. S.; Yoon, N. M.; Nazer, B. J. Org. Chem. 1987, 52, 5400.
3. (c) Cha, J. S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301, 313.
4. (d) Cha, J. S.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Bull. Korean Chem. Soc. 1988, 9, 384.
5. (e) Cha, J. S. Org. Prep. Proced. Int. 1989, 21, 451.
6. (f) Cha, J. S.; Yoon, M. S.; See, J. B.; Kim, J. M. Bull. Korean Chem. Soc. 1990, 11, 76.
7. (g) Cha, J. S.; Lee, J. C.; Lee, H. S.; Lee, S. E. Org. Prep. Proced. Int. 1992, 24, 327.
8. (h) Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670.
9. (i) Cha, J. S.; Lee, K. D.; Kwon, O. O.; Kim, J. M.; Lee, H. S. Bull. Korean Chem. Soc. 1995, 16, 561.
10. (j) Cha, J. S.; Chang, S. W.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Org. Prep. Proced. Int. 1997, 29, 665.
11. (a) Brown, H. C.; McFarlin, R. F. J. Am. Chem. Soc. 1956, 78, 252.; 1958, 80, 5372.
12. (a) Brown, H. C.; McFarlin, R. F. J. Am. Chem. Soc. 1956, 78, 252.; 1958, 80, 5372.
13. (b) Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1958, 80, 5377.
14. (c) Brown, H. C.; Krishnamurthy, S. Tetrahedron Lett. 1979, 35, 567.
15. (d) Babler, J. H.; Invergo, B. J. Tetrahedron Lett. 1981, 22, 11.
16. (e) Babler, J. H. Synth. Commun. 1982, 12, 839.
17. (f) Cha, J. S.; Brown, H. C. J. Org. Chem. 1993, 58, 4732.
18. (a) Weissman, P. M.; Brown, H. C. J. Org. Chem. 1966, 31, 282.
19. (b) Zakharkin, L. I.; Khorlina, I. M. Tetrahedron Lett. 1962, 619.
20. (c) Zakharkin, L. I.; Khorlina, I. M. Izv. Akad. Nauk. SSSR, Ser. Khim. 1964, 465.
21. (d) Muraki, M.; Mukaiyama, T. Chemistry Lett. 1975, 215.
22. (e) Yoon, N. M.; Shon, Y. S.; Ahn, J. H. Bull. Korean Chem. Soc. 1992, 13, 199.
23. (f) Yoon, N. M.; Ahn, J. H.; An, D. K. Bull. Korean Chem. Soc. 1992, 13, 339.
24. (g) Yoon, N. M.; Ahn, D. K.; Shon, Y. S. J. Org. Chem. 1993, 58, 1941.
25. (h) Cha, J. S.; Min, S. J.; Lee, J. C.; Lee, H. S.; Lee, S. E. Org. Prep. Proced. Int. 1992, 24, 359.
26. (i) Cha, J. S.; Kim, J. M.; Jeoung, M. K.; Kwon, O. O.; Kim, E. J. Org. Prep. Proced. Int. 1995, 27, 95.
27. (a) Wittig, G.; Hornberger, F. Ann. 1952, 577, 11.
28. (b) Ried. W.; Konigstein, F. J. Angew. Chem. 1958, 70, 165.
29. (c) Staab, H. A.; Brauning, H. Ann. 1962. 654, 119.
30. (d) Brown, H. C.; Tsukamoto, A. J. Am. Chem. Soc. 1961, 83, 4549.
31. (e) Weygand, F.; Eberhardt, G. Angew. Chem. 1952, 64, 458.
32. (f) Zakharkin, L. I.; Maslin, D. N.; Gavrilenko, V. V. Tetrahedron 1969, 25, 5555.
33. (g) Brown, H. C.; Tsukamoto, A. J. Am. Chem. Soc. 1964, 86, 1089.
34. (h) Muraki, M.; Mukaiyama, T. Chemistry Lett. 1975, 875.
35. (i) Yoon, N. M.; Gyoung, Y. S. Bull. Korean Chem. Soc. 1992, 13, 341.
36. (j) Cha, J. S.; Lee, J. C.; Kim, S. E.; Kwon, O. O.; Kim, J. M.; Lee, H. S.; Min, S. J. Tetrahedron Lett. 1991, 32, 6903.
37. (k) Cha, J. S.; Lee, J. C.; Lee, S. E.; Lee, H. S. Bull. Korean Chem. Soc. 1991, 12, 598.
38. (l) Cha, J. S.; Lee, S. E.; Lee, H. S.; Lee, J. C.; Kim, J. M.; Kwon, O. O.; Min, S. J. Bull. Korean Chem. Soc. 1992, 13, 338.
39. (m) Cha, J. S.; Kim, J. M.; Jeoung, M. K. Bull. Korean Chem. Soc. 1994, 15, 708.
40. (a) Brown, H. C.; Schoaf, C. J.; Garg, C. P. Tetrahedron Lett. 1959, 9.
41. (b) Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1964, 86, 1079, 1085.
42. (c) de Peretti, D.; Strzalko-Bottin, T.; Seydenpenne, J. Bull. Soc. Chim. Fr. 1974, 2925.
43. (d) Zakharkin, L. I.; Khorlina, I. M. Dokl. Akad. Nauk. SSSR, 1957, 116, 422.
44. (e) Miller, A. E. G.; Bliss, J. W.; Sehwartzman, L. H. J. Org. Chem. 1959, 24, 627.
45. (f) Caton, M. P. L.; Coffee, E. C. J.; Watkins, G. L. Tetrahedron Lett. 1974, 585.
46. (g) Yoon, N. M.; Kim, S. K.; Gyong, Y. S. Bull. Korean Chem. Soc. 1986, 7, 323.
47. (h) Cha, J. S.; Oh, S. Y.; Kim, J. E. Bull. Korean Chem. Soc. 1987, 8, 301.
48. (i) Cha, J. S.; Yoon, M. S. Tetrahedron Lett. 1989, 30, 3677.
49. (j) Cha, J. S.; Lee, S. E.; Lee, H. S. Org. Prep. Proced. Int. 1992, 24, 331.
50. (k) Cha, J. S. Bull. Korean Chem. Soc. 1992, 13, 670.
51. (l) Cha, J. S.; Jeoung, M. K.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Org. Prep. Proced. Int. 1994, 26, 552.
52. (m) Yoon, N. M.; An, D. K.; Jeong, K. H. Bull. Korean Chem. Soc. 1993, 14, 302.
53. (n) Cha, J. S.; Kwon, O. O.; Jeoung, M. K.; Kim, E. J. Bull. Korean Chem. Soc. 1994, 15, 1021.
54. (o) Cha, J. S.; Chang, S. W.; Kwon, O. O.; Kim, J. M. Synlett 1996, 165.
55. Cha, J. S.; Kim, J. E.; Lee, K.W.J Org. Chem. 1987, 52, 5030.
56. Cha, J. S.; Oh, S. Y.; Lee, K. W.; Yoon, M. S.; Lee, J. C. Hetetocycles 1988, 27, 1595.
57. (a) Brown, H. C.; Rao, C. G.; Kulkarni, S. U. Synthesis 1979, 704.
58. (b) Cha, J. S.; Kim, J. M.; Kwon, O. O.; Lee, J. C. Bull. Korean Chem. Soc. 1998, 19, 1301.
59. (c) Cha, J. S.; Chun, J. H.; Kim, J. M.; Kwon, O. O.; Kwon, S. Y.; Lee, J. C. Bull. Korean Chem. Soc. 1999, 20, 400.
60. (d) Cha, J. S.; Lee, D. Y.; Kim, J. M. Org. Prep. Proced. Int. 1999, 31, 694.
61. (a) Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1998, 19, 1301.
62. (b) Cha, J. S.; Chun, J. H.; Kim, J. M.; Lee, D. Y.; Cho, S. D. Bull. Korean Chem. Soc. 1999, 20, 1373.
63. (a) Cha, J. S.; Kim, J. M.; Chun, J. H.; Kwon, O. O.; Kwon, S. Y.; Han, S. W. Org. Prep. Proced. Int. 1999, 31, 204.
64. (b) Cha, J. S.; Chun, J. H. Bull. Korean Chem. Soc. 2000, 21, 375.
65. Cha, J. S.; Park, J. H.; Lee, D. Y. Bull. Korean Chem. Soc. 2001, 22, 325.
66. Cho, B. T.; Yoon, N. M. Bull. Korean Chem. Soc. 1982, 3, 149.
67. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786.
68. Yoon, N. M.; Cho, B. T. Tetrahedron Lett. 1982, 23, 2475.
69. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. Organic Synthesis via Boranes; Wiley-Interscience: New York, 1975.
70. In the case of Na salts of aliphatic carboxylic acid, the reaction temperature should be maintained below 15 °C; the yields of aldehydes drops significantly above that temperature.
71. The oxidation requires 3 hrs under reflux or 12 hrs at room temperature for the aliphatic series; 6 hrs at room temperature for the aromatic series.
72. The oxidation requires 3 hrs under reflux or 12 hrs at room temperature.