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

HRID 2174546Notes

Reaction equation

HRID 2174546 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4b02df124b95422e9b371cdf0d9bdced
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

Loading…