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

HRID 2174546ノート

反応式

HRID 2174546 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b02df124b95422e9b371cdf0d9bdced
出典データセット
uspto-grants-2015_06
特許番号
US09061998B2

反応ノート

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