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Volumn , Issue 20, 2009, Pages 3352-3354

Facile preparation of CF3-Containing 1-bromoallenes

Author keywords

Alkynes; Allenes; Bromination; Fluorine; Trifluoromethyl

Indexed keywords

1 BROMOALLENE DERIVATIVE; ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; BROMINE DERIVATIVE; CARBON TETRABROMIDE; FLUOROCARBON; ORGANIC SOLVENT; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

EID: 72149121807     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218383     Document Type: Article
Times cited : (19)

References (27)
  • 5
    • 33746885539 scopus 로고    scopus 로고
    • Other examples of trifluoromethylinfstituted allenes
    • Yamazaki, T.; Yamamoto, T.; Ichihara, R. J. Org. Chem 2006, 71, 6251. Other examples of trifluoromethylinfstituted Allenes.
    • (2006) J. Org. Chem. , vol.71 , pp. 6251
    • Yamazaki, T.1    Yamamoto, T.2    Ichihara, R.3
  • 17
    • 72149133289 scopus 로고    scopus 로고
    • Krause N.; Hashmi A. S. K., Eds.
    • Modern Allene Chemistry, Vol. 1 and 2; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004.
    • (2004) Modern Allene Chemistry , vol.1-2
  • 25
    • 72149126616 scopus 로고    scopus 로고
    • note
    • Procedure for the Preparation of the Allenylcarbinols 7a and 7b To a solution of 3a (0.32 g, 1.20 mmol) and isobutyraldehyde (142 mL, 1.6 mmol) in Et2O (5 mL) was added BuLi (0.98 mL, 1.6 mmol, 1.6 M in hexane) at 105 C. The solution was stirred at that temperature for 2 h. The reaction mixture was quenched with 1 M aq HCl solution (3 mL) and extracted with EtOAc (3 20 mL). Usual workup and purification by silica gel chromatography (hexaneEtOAc, 12:1) afforded 7a (0.087 g, 0.41 mol 34%) and 7b (0.14 g, 0.66 mmol 55%). Compound 7a: colorless oil. Rf = 0.56 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.01 (d, J = 6.9 Hz, 6 H), 1.80 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.5 Hz, 1 H), 6.73 (qd, J = 3.3, 1.5 Hz, 1 H), 7.267.38 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.0, 19.5, 32.7,73.8, 103.0, 106.0 (q, J = 32.3 Hz), 123.1 (q, J = 274.1 Hz), 127.4, 128.6, 129.0, 131.1, 204.4 (q, J = 4.4 Hz). 19F NMR (283 MHz, CDCl3): d = 62.44 (s). IR (neat): 692, 721, 747, 828, 920, 1001, 1029, 1074, 1127, 1210, 1273, 1369, 1387, 1411, 1462, 2874, 2934, 2963, 3429 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1176. Compound 7b: colorless oil. Rf = 0.47 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.00 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.6 Hz, 3 H), 1.88 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.2 Hz, 1 H), 6.78 (qd, J = 3.3, 1.5 Hz, 1 H), 7.277.39 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.1, 19.6, 32.8, 73.6, 103.2, 106.1 (q,J = 32.2 Hz), 123.2 (q, J = 272.9 Hz), 127.6, 128.6, 129.0, 131.1, 204.1 (q, J = 4.3 Hz). 19F NMR (283 MHz, CDCl3): d = 62.52 (s). IR (neat): 692, 719, 747, 829, 920, 1000, 1029, 1074, 1123, 1210, 1274, 1369, 1388, 1411, 1462, 1715, 1961, 2876, 2933, 2967, 3036, 3410 cm1. HRMS FAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1187.
  • 26
    • 72149108933 scopus 로고    scopus 로고
    • note
    • Procedure for the Preparation of the Allenylcarbinols 7a and 7b To a solution of 3a (0.32 g, 1.20 mmol) and isobutyraldehyde (142 mL, 1.6 mmol) in Et2O (5 mL) was added BuLi (0.98 mL, 1.6 mmol, 1.6 M in hexane) at 105 C. The solution was stirred at that temperature for 2 h. The reaction mixture was quenched with 1 M aq HCl solution (3 mL) and extracted with EtOAc (3 20 mL). Usual workup and purification by silica gel chromatography (hexaneEtOAc, 12:1) afforded 7a (0.087 g, 0.41 mol 34%) and 7b (0.14 g, 0.66 mmol 55%). Compound 7a: colorless oil. Rf = 0.56 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.01 (d, J = 6.9 Hz, 6 H), 1.80 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.5 Hz, 1 H), 6.73 (qd, J = 3.3, 1.5 Hz, 1 H), 7.267.38 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.0, 19.5, 32.7,73.8, 103.0, 106.0 (q, J = 32.3 Hz), 123.1 (q, J = 274.1 Hz), 127.4, 128.6, 129.0, 131.1, 204.4 (q, J = 4.4 Hz). 19F NMR (283 MHz, CDCl3): d = 62.44 (s). IR (neat): 692, 721, 747, 828, 920, 1001, 1029, 1074, 1127, 1210, 1273, 1369, 1387, 1411, 1462, 2874, 2934, 2963, 3429 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1176. Compound 7b: colorless oil. Rf = 0.47 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 1.00 (d, J = 6.6 Hz, 3 H), 1.01 (d, J = 6.6 Hz, 3 H), 1.88 (br s, 1 H), 1.96 (oct, J = 6.6 Hz, 1 H), 4.12 (dd, J = 6.6, 1.2 Hz, 1 H), 6.78 (qd, J = 3.3, 1.5 Hz, 1 H), 7.277.39 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 17.1, 19.6, 32.8, 73.6, 103.2, 106.1 (q,J = 32.2 Hz), 123.2 (q, J = 272.9 Hz), 127.6, 128.6, 129.0, 131.1, 204.1 (q, J = 4.3 Hz). 19F NMR (283 MHz, CDCl3): d = 62.52 (s). IR (neat): 692, 719, 747, 829, 920, 1000, 1029, 1074, 1123, 1210, 1274, 1369, 1388, 1411, 1462, 1715, 1961, 2876, 2933, 2967, 3036, 3410 cm1. HRMS FAB: m/z calcd for C14H16OF3 [M + H]+: 257.1153; found: 257.1187.
  • 27
    • 72149127580 scopus 로고    scopus 로고
    • note
    • Procedure for the Preparation of the 2,5-Dihydrofuran 8a To a solution of 7a (0.087 g, 0.41 mmol) in acetone (3 mL) was added AgNO3 (12 mg, 0.082 mmol) at r.t. The solution was protected from light and stirred at that temperature for 4 d. Concentration by rotary evaporator furnished a crude mixture that was purified by silica gel chromatography (hexaneEtOAc, 20:1) to afford 8a (0.066 g, 75%) as a pale yellow oil; Rf = 0.77 (hexaneEtOAc, 4:1). 1H NMR (300 MHz, CDCl3): d = 0.94 (d, J = 6.9 Hz, 3 H), 1.13 (d, J = 6.9 Hz, 3 H), 2.03 (septd, J = 6.6, 1.2 Hz, 1 H), 5.18 (dq, J = 6.6, 0.9 Hz, 1 H), 5.835.88 (m, 1 H), 6.45 (sext, J = 1.8 Hz, 1 H), 7.267.44 (m, 5 H). 13C NMR (75.5 MHz, CDCl3): d = 14.5, 19.9, 32.0, 87.7 (q, J = 0.6 Hz), 89.3 (q, J = 0.6 Hz), 121.7 (q, J = 269.2 Hz), 126.4, 128.4, 128.7, 131.9 (q, J = 33.5 Hz), 135.8 (q, J = 4.4 Hz), 140.0. 19F NMR (283 MHz, CDCl3): d = 64.13 (s). IR (neat): 698, 726, 760, 879, 917, 1009, 1051, 1068, 1126, 1158, 1242, 1265, 1281, 1334, 1360, 2876, 2935, 2970 cm1. HRMSFAB: m/z calcd for C14H16OF3 [M]+: 256.1075; found: 256.1046.


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