Methanol → HCID 178501147, compound

HRID 1482885Notes

Reaction equation

HRID 1482885 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)=[O:4].B.CSC.CO>C1COCC1>[OH:12][CH2:11][C@H:8]1[CH2:7][CH2:6][C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 178501163HCID 178501163, compound

Product 1

HCID 178501147HCID 178501147, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (5.00 g, 26.9 mmol) in THF (30 mL) was added borane-dimethylsulfide complex (1.0 M in THF, 40 mL, 40 mmol) dropwise at 0° C. and then the mixture was stirred at 20° C. for 6 hours. Methanol (50 mL) was dropwise at 0° C., and then the reaction mixture was stirred at room temperature for 1 hour before being concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate. MS ESI calc'd for C9H12O3 [M+H]+ 173. found 173. 1H NMR: (400 MHz, DMSO-d6) δ 4.39 (br s, 1H), 3.57 (s, 3H), 3.21-3.18 (m, 2H), 2.22-2.20 (m, 1H), 1.91-1.87 (m, 2H), 1.74-1.73 (m, 2H), 1.31-1.27 (m, 3H), 0.91-0.76 (m, 2H).

Workup

  1. customwas dropwise at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. concentrationbefore being concentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-a1adcedaed364f4abeff444be87a38c8
Source dataset
uspto-grants-2016_08
Patent number
US09416111B2

Reaction notes

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