4-(Benzyloxy)-3-(trifluoromethyl)benzoic acid → (4-Benzyloxy-3-trifluoromethylphenyl)methanol

HRID 19939노트

반응식

HRID 19939 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[C:18]([F:19])([F:21])[F:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 167490234-(Benzyloxy)-3-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 16749447(4-Benzyloxy-3-trifluoromethylphenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

4-Benzyloxy-3-trifluoromethyl-benzoic acid (CAB03046, 3.555 g, 12 mmol) in THF (20 mL) was added dropwise to a suspension of lithium aluminum hydride (1.0 g, 26.3 mmol) in THF (20 mL). The mixture was stirred for another 30 minutes at room temperature and then quenched by addition of 2N NaOH (5 mL). The white precipitate was filtered off and washed with dichloromethane (100 mL), the filtrate was dried over sodium sulphate and concentrated under reduced pressure. The resulting oil was crystallised from diethyl ether/hexane. Yield: 3.31 g (98%). 1H-NMR (400 MHz, CDCl3)=1.72 (t, J=5.9 Hz, 1H, —OH), 4.66 (d, J=5.9 Hz, 2H, —CH2OH), 5.21 (s, 2H, —CH2Ph), 7.02 (d, J=8.2 Hz, 1H), 7.30-7.48 (m, 6H), 7.61 (d, J=2.3 Hz, 1H). LRMS (FAB+): 91.1 (100), 265.2 (45), 282.2 (40, [M+H]+.

후처리

  1. customquenched by addition of 2N NaOH (5 mL)
  2. filtrationThe white precipitate was filtered off
  3. washwashed with dichloromethane (100 mL)
  4. dry with materialthe filtrate was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oil was crystallised from diethyl ether/hexane

출처 및 근거

ORD 기록
ord-c13885aa43784e799265b8210021ee3e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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