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

HRID 14315

Reaction equation

HRID 14315 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].C(O)(=O)C.O>O1CCCC1>[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

4

Reactant 2

HCID 2968504-(Methoxycarbonyl)cyclohexane-1-carboxylic acidHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold, stirred solution of acid from step 1 (700 mg, 3.8 mmol) in tetrahydrofuran (10 mL) was added borane-dimethyl sulfide complex (2 mL, 4.1 mmol). The reaction mixture was warmed to room temperature for 2 h and a 1:1 mixture of acetic acid/water (10 mL) was added. The resulting mixture was concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate) provided methyl 4-(hydroxymethyl)cyclohexanecarboxylate (560 mg): 1H NMR (500 MHz, CDCl3) δ 3.68 (s, 3H), 3.51-3.46 (m, 2H), 2.59-2.57 (m, 1H), 2.05-2.00 (m, 2H), 1.65-1.55 (m, 5H), 1.31-1.27 (m, 2H).

Workup

  1. additionwas added borane-dimethyl sulfide complex (2 mL, 4.1 mmol)
  2. additionwas added
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customPurification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-4a51cdcba1f6402d89150c3f00c2a8ad
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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