4-Methoxybenzyl alcohol → (R)-1,1,1-Trifluoro-3-[(4-methoxybenzyl)oxy]-2-propanol

HRID 420317노트

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HRID 420317 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[CH2:13]1[O:15][C@H:14]1[C:16]([F:19])([F:18])[F:17]>C1COCC1.O>[F:17][C:16]([F:19])([F:18])[C@H:14]([OH:15])[CH2:13][O:10][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 7016923(2R)-2-(trifluoromethyl)oxirane

생성물 1

HCID 66649618(R)-1,1,1-Trifluoro-3-[(4-methoxybenzyl)oxy]-2-propanol

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a suspension of NaH (390 mg, 8.9 mmol, 55% in mineral oil) in THF (10 mL) at 0° C. was added 4-methoxybenzylalcohol (1.27 g, 8.92 mmol) in THF (5 mL). After 1 h stirring at 0° C. R-(+)-3,3,3-trifluoro-1,2-epoxypropane (500 mg, 4.46 mmol) was added to a 20 mL microwave vial via syringe. The closed vial was heated at 100° C. for 18 h. The reaction mixture was diluted with water and extracted twice with Et2O. The organic phase was washed with brine, dried over MgSO4, filtered and evaporated. Chromatography over silica (cyclohexane-EtOAc 95:5 to cyclohexane-EtOAc 75:25) afforded the title compound: ESIMS [M+NH4]+=268; 1H NMR (360 MHz, CDCl3): δ 7.29 (d, 2H), 6.94 (d, 2H), 4.56 (s, 2H), 4.15 (m, 1H), 3.87 (s, 3H), 3.74 (dd, 1H), 3.66 (dd, 1H), 2.88 (d, 1H).

후처리

  1. temperatureThe closed vial was heated at 100° C. for 18 h
  2. extractionextracted twice with Et2O
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-9839d77ad6414c189dca7fe7b151aff4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093406B2

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