1-(4-Bromophenyl)cyclopentanecarboxylic acid → [1-(4-Bromophenyl)cyclopentyl]methanol

HRID 2174546노트

반응식

HRID 2174546 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:13](O)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:13][OH:14])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8249921-(4-Bromophenyl)cyclopentanecarboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 67480063[1-(4-Bromophenyl)cyclopentyl]methanol수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-(4-bromophenyl)cyclopentanecarboxylic acid (Enamine, 1 g, 3.72 mmol) in tetrahydrofuran (10 mL), at 0° C. was added slowly LiAlH4 1M/THF (7.43 mL, 7.43 mmol). The reaction mixture was stirred at room temperature for 1 h and quenched by water. The product was extracted with DCM and the organic layer was evaporated under reduced pressure. The product was purified on silica gel column chromatography using a cyclohexane to cyclohexane/EtOAc 70:30 as eluant. The appropriate fractions were combined and concentrated in vacuo to give the title product (1-(4-bromophenyl)cyclopentyl)methanol (832 mg, 3.26 mmol, 88% yield) as a colourless oil. 1H NMR: (DMSO-d6, 300 MHz) δ 7.40 (m, 2H), 7.25 (m, 2H), 4.65 (m, 1H), 3.38 (m, 2H), 1.95 (m, 2H), 1.65 (m, 6H).

후처리

  1. customquenched by water
  2. extractionThe product was extracted with DCM
  3. customthe organic layer was evaporated under reduced pressure
  4. customThe product was purified on silica gel column chromatography
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4b02df124b95422e9b371cdf0d9bdced
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061998B2

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