Triethylamine → (R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

HRID 1195091

반응식

HRID 1195091 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C@H:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl>[F:18][C:19]([F:28])([F:29])[C@H:20]([O:27][C:13](=[O:14])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

생성물 1

HCID 22850730(R)-(+)-1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate수율 65.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 5 ml of a methylene chloride solution containing 0.56 g of 4-benzyloxybenzoic acid chloride was slowly added a solution of 0.38 g of (R)-(+)-1-trifluoromethylheptanol and 0.23 g of triethylamine in 5 ml of methylene chloride under ice-cooling. The mixture was allowed to warm to room temperature and stirred at that temperature for 12 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride phase was washed successively with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residual crude product was purified by silica gel column chromatography to obtain 0.53 g of (R)-(+)-4-benzyloxybenzoic acid 1-trifluoromethylheptyl ester.

후처리

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride phase was washed successively with diluted hydrochloric acid, water
  4. dry with materialan aqueous 1N sodium carbonate solution, and water and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customthe residual crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-58a09efc368340d4a7a3508279458c22
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110497

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