4-(Methoxycarbonyl)cyclohexane-1-carboxylic acid → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 539313Notes

Reaction equation

HRID 539313 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)=[O:4]>C1COCC1>[OH:12][CH2:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]1

Participants

3

Reactant 1

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acid

Product 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(methoxycarbonyl)cyclohexanecarboxylic acid (5.44 g, 29.2 mmol) in dry THF at −78° C., was added borane-methyl sulfide complex (19.0 mL, 38.0 mmol) dropwise over 20 min. The mixture was stirred for 3 h and was then allowed to slowly attain r.t. The reaction was quenched with water (20 mL) and the mixture was extracted with EtOAc. The organic phase was washed once with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (4.80 g, 95% yield) as a mixture of two diastereomers: MS (EI) m/z 172 M+.

Workup

  1. customwas then allowed to slowly attain r.t
  2. customThe reaction was quenched with water (20 mL)
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic phase was washed once with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-777a4cb3223f482d9671a5ade8c9255d
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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