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

HRID 21423

반응식

HRID 21423 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].CN(C1C=CC=CN=1)C.C(N(CC)CC)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 61.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml), under ice cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g).

후처리

  1. waitThe mixture was left
  2. customThe methylene chloride layer separated
  3. washwas washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order
  4. dry with materialdried over magnesium sulfate
  5. distillationdistilled
  6. customto obtain a crude objective compound
  7. customThe compound was purified by toluene/silica gel chromatography and recrystallization from ethanol

출처 및 근거

ORD 기록
ord-b0bbf4059f3f4f6985f90088f6ed8e04
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424005

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