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Volumn , Issue 2, 2007, Pages 283-287

Deprotection of acetals and ketals in a colloidal suspension generated by sodium tetrakis(3,5-trifluoromethylphenyl)borate in water

Author keywords

Acetals; Hydrolysis; Phase transfer catalysis; Protecting groups; Sodium

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 2 PHENYL 1,3 DIOXOLANE; ACETAL DERIVATIVE; BORIC ACID; SODIUM TETRAKIS(3,5 TRIFLUOROMETHYLPHENYL)BORATE; UNCLASSIFIED DRUG; WATER;

EID: 33847010230     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968009     Document Type: Article
Times cited : (24)

References (37)
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    • Typical Procedure for Hydrolysis: A mixture of NaBAr F4x2H2O (5 × 10-3 mmol) 11 and acetal (5.0 mmol) in H2O (10 mL) was placed in a 25-mL flask. The resulting suspension was stirred vigorously at 30°C for a certain period as shown in Table 2. After the completion of the reaction, the reaction mixture was extracted with CH2Cl2 2 x 5 mL, The extracts were dried and filtered through a short column of silica gel to remove the sodium salt. Upon concentration, the desired carbonyl products were obtained in pure form. For all products reported in Table 2, full 1H and 13C NMR data were compared with those of the pure sample obtained from commercial sources, or with reported data.25
    • 25
  • 16
    • 33847043083 scopus 로고    scopus 로고
    • Spectral Data for the Hydrolyzed Products: 1,2-O- Isopropylidene-α-d-glucofuranose:18 mp 154-158°C (dec, 1H NMR (400 MHz, D2O, δ, 5.90 (d, J, 4 Hz, 1 H, 4.58 (d, J, 4 Hz, 1 H, 4.20 (s, 1 H, 3.97 (d, J, 8 Hz, 1 H, 3.78 (m, 1 H, 3.68 (d, J, 12 Hz, 1 H, 3.97 (d, J, 8 Hz, 1 H, 3.52 (dd, J, 6 Hz, 1 H, 1.39 (s, 3 H, 1.24 (s, 3 H, 13C NMR (100 MHz, D2O, δ, 112.5 (C, 104.6 (CH, 84.3 (CH, 79.6 (CH, 78.6 (CH, 68.2 (CH, 63.4 (CH2, 25.4 (CH3, 25.0 (CH3, 4-Propylbenzaldehyde: 21 1H NMR (400 MHz, CDCl3, δ, 9.98 (s, 1 H, 7.81 (d, J, 6.8 Hz, 2 H, 7.34 (d, J, 6.8 Hz, 2 H, 2.68 (t, J, 7 Hz, 2 H, 1.68 (m, 2 H, 0.96 (t, J, 7 Hz, 3 H, 13C NMR (100 MHz, CDCl3, δ, 191.64 (CH, 150.1 C
    • 3).
  • 17
    • 0035945077 scopus 로고    scopus 로고
    • Acetals 1, 6, 7, 8, 9, 10, 11, 15, 17, 18 and 19 were synthesized according to the literature methods. Other acetals were obtained from commercial sources: (a) Compound 1: Mosca, R.; Fagnoni, M.; Mella, M.; Albini, A. Tetrahedron 2001, 57, 10319.
    • Acetals 1, 6, 7, 8, 9, 10, 11, 15, 17, 18 and 19 were synthesized according to the literature methods. Other acetals were obtained from commercial sources: (a) Compound 1: Mosca, R.; Fagnoni, M.; Mella, M.; Albini, A. Tetrahedron 2001, 57, 10319.
  • 18
    • 0029561102 scopus 로고    scopus 로고
    • Compounds 6 and 7: Barluenga, J.; del Pozo, C.; Olano, B. Synthesis 1995, 1529.
    • (b) Compounds 6 and 7: Barluenga, J.; del Pozo, C.; Olano, B. Synthesis 1995, 1529.
  • 19
    • 0034549054 scopus 로고    scopus 로고
    • Compound 8: Eash, K. J.; Pulia, M. S.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2000, 65, 8399.
    • (c) Compound 8: Eash, K. J.; Pulia, M. S.; Wieland, L. C.; Mohan, R. S. J. Org. Chem. 2000, 65, 8399.
  • 20
    • 0031954895 scopus 로고    scopus 로고
    • Compound 9: Walton, R.; Lahti, P. M. Synth. Commun. 1998, 28, 1087.
    • (d) Compound 9: Walton, R.; Lahti, P. M. Synth. Commun. 1998, 28, 1087.
  • 21
    • 0011961060 scopus 로고    scopus 로고
    • Compound 10: Bořkovec, A. B. J. Org. Chem. 1961, 26, 4866.
    • (e) Compound 10: Bořkovec, A. B. J. Org. Chem. 1961, 26, 4866.
  • 22
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    • Compound 11: Sulzbacher, M.; Bergmann, E.; Pariser, E. R. J. Am. Chem. Soc. 1948, 70, 2827.
    • (f) Compound 11: Sulzbacher, M.; Bergmann, E.; Pariser, E. R. J. Am. Chem. Soc. 1948, 70, 2827.
  • 23
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    • Compound 15: Goud, P. M.; Venkatachalam, T. K.; Uckun, F. M. Synth. Commun. 2003, 33, 1185.
    • (g) Compound 15: Goud, P. M.; Venkatachalam, T. K.; Uckun, F. M. Synth. Commun. 2003, 33, 1185.
  • 24
    • 33845281070 scopus 로고    scopus 로고
    • Compound 17: Ouchi, M.; Inoue, Y.; Wada, K.; Iketani, S.; Hakushi, T.; Weber, E. J. Org. Chem. 1987, 52, 2420.
    • (h) Compound 17: Ouchi, M.; Inoue, Y.; Wada, K.; Iketani, S.; Hakushi, T.; Weber, E. J. Org. Chem. 1987, 52, 2420.
  • 25
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    • Compound 18: Carroll, F. I.; Berrang, B. D.; Linn, C. P. J. Heterocycl. Chem. 1981, 18, 941.
    • (i) Compound 18: Carroll, F. I.; Berrang, B. D.; Linn, C. P. J. Heterocycl. Chem. 1981, 18, 941.
  • 26
    • 0013311725 scopus 로고    scopus 로고
    • Compound 10: Lai, J.-Y.; Shi, X.-X.; Dai, L.-X. J. Org. Chem. 1992, 57, 3485.
    • (j) Compound 10: Lai, J.-Y.; Shi, X.-X.; Dai, L.-X. J. Org. Chem. 1992, 57, 3485.
  • 27
    • 33847082071 scopus 로고    scopus 로고
    • Preparation of 20: A solution of 17 (0.32 g, 2 mmol) and Et3N (0.38 mL, 2.8 mmol) in anhyd CH2Cl2 (5 mL) was cooled in an ice-water bath under dried nitrogen. Chlorotrimethylsilane (0.31 mL, 2.4 mmol) was slowly added to the above solution with stirring. After the addition, the resulting mixture was heated to reflux for 6 h. The mixture was filtered to remove the ammonium salt and the filtrate was evaporated under reduced pressure to remove the excess amine and chlorotrimethylsilane. The residue was dissolved in CH2Cl2 (10 mL) and washed with sat. NaHCO3. The organic extract was dried over MgSO4 and concentrated to give the desired compound 20 (0.46 g, 100, 1H NMR (400 MHz, CDCl3, δ, 3.64 (d, J, 12 Hz, 2 H, 3.55 (s, 2 H, 3.52 (d, J, 12 Hz, 2 H, 1.41 (s, 3 H, 1.37 (s, 3 H, 0.79 (s, 3 H, 0.09 (s, 9 H, 13C NMR 100 MHz, CDCl
    • 3Si: C, 56.85; H, 10.41. Found: C, 56.77; H, 10.21.
  • 32
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    • Mixed Surfactant Systems
    • Holland, P. M, Rubingh, D. N, Eds, American Chemical Society: Washington, DC
    • (b) Holland, P. M.; Rubingh, D. N. In Mixed Surfactant Systems; Holland, P. M.; Rubingh, D. N., Eds.; ACS Symposium Series 501, American Chemical Society: Washington, DC, 1992, 2.
    • (1992) ACS Symposium Series , vol.501 , pp. 2
    • Holland, P.M.1    Rubingh, D.N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.