Triethylamine → Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester

HRID 1590014

반응식

HRID 1590014 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.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:27][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:19]([F:18])([F:28])[F:29])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 2779099(R)-(+)-1,1,1-Trifluoro-2-octanolHCID 37664104-Benzyloxybenzoylchloride

생성물 1

HCID 14549213Benzoic acid, 4-(phenylmethoxy)-, 1-(trifluoromethyl)heptyl ester수율 63.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

In 20 ml of methylene chloride was dissolved 1.1 g of 4-benzyloxybenzoic acid chloride, and to the solution was slowly added a solution of 0.74 g of (R)-(+)-1,1,1-trifluoro-2-octanol ([α]D20 =+25.2°), 0 4 g of triethylamine, and a catalytic amount of dimethylaminopyridine in 10 ml of methylene chloride under ice-cooling. After warming to room temperature, the solution was stirred for 12 hours. The reaction mixture was poured into ice-water and extracted with methylene chloride. The methylene chloride phase was successively washed with diluted hydrochloric acid, water, an aqueous 1N sodium carbonate solution, and water and then 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 1.0 g of 1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate.

후처리

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

출처 및 근거

ORD 기록
ord-22895893583640bfabf2294645029065
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05202054

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