Methanol → 5-Benzyloxypent-2-yl acetate

HRID 1919768Notes

Reaction equation

HRID 1919768 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][CH2:16][CH2:17][CH2:18]C(O)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO>N1C=CC=CC=1>[C:5]([O:4][CH:1]([CH2:18][CH2:17][CH2:16][O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 117455305-(Benzyloxy)pentan-2-ol

Product 1

HCID 592348995-Benzyloxypent-2-yl acetateYield 36%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (1.86 mL) was added to a mixed solution of 5-benzyloxypentan-2-ol (957 mg, 4.93 mmol) in pyridine (1.8 mL) in an ice bath. After completion of the reaction, methanol (1.6 mL) was added to the reaction solution in an ice bath, and the solvent was evaporated. The pH was adjusted to 4 with 2 mol/L hydrochloric acid. After extraction with chloroform-water, the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 420 mg of the title compound (yield: 36%) as a colorless oil.

Workup

  1. additionwas added to the reaction solution in an ice bath
  2. customthe solvent was evaporated
  3. extractionAfter extraction with chloroform-water
  4. washthe organic layer was washed with a saturated sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6412981c89f744c88a57670617327dd6
Source dataset
uspto-grants-2012_05
Patent number
US08168666B2

Reaction notes

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