Methanol → HCID 178500705, compound

HRID 1028201Notes

Reaction equation

HRID 1028201 reaction equation
CO.[CH3:3][O:4][C:5](=[O:14])[CH2:6][CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1.[BH4-].[Na+]>[Cl-].[NH4+]>[CH3:3][O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][CH2:8]1.[CH3:3][O:4][C:5](=[O:14])[CH3:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 21249113Methyl 2-(4-oxocyclohexyl)acetate

Product 2

HCID 6584Methyl AcetateYield 12%HCID 178500705HCID 178500705, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a methanol (50 mL) solution of (4-oxo-cyclohexyl)-acetic acid methyl ester (4.18 g) obtained in Example (1c), sodium borohydride (1.86 g) was added in small portions at 0° C. The reaction mixture was stirred for 1 hour and diluted with a 10% aqueous ammonium chloride solution (100 mL). The organic solvent was removed using an evaporator. The remaining aqueous solution was subjected to two extractions with ethyl acetate. The organic layer was washed with saturated brine, then dried over sodium sulfate, and then concentrated to obtain trans-(4-hydroxy-cyclohexyl)-acetic acid methyl ester (2.56 g, 60%) as a colorless oil and cis-4-hydroxy-cyclohexyl)-acetic acid methyl ester (0.517 g, 12%) as a colorless oil.

Workup

  1. customThe organic solvent was removed
  2. customan evaporator
  3. extractionThe remaining aqueous solution was subjected to two extractions with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4684c1b85a14155b25f0b7dc763c42e
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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