Water → Ethyl alpha-hydroxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetate

HRID 617397Notes

Reaction equation

HRID 617397 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[BH4-].[Na+].O>CO>[OH:1][CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 15390471HCID 15390471, compound

Product 1

HCID 18357802Ethyl alpha-hydroxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-oxo-2-[2-(tetrahydropyran-2-yloxymethyl)phenyl]acetate (22.60 g, 77.3 mmol) in methanol (20 ml) was stirred at 0° C., and sodium borohydride (1.46 g, 38.6 mmol) was added to thereto. After 10 minutes, water (100 ml) was added, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1) to give the desired compound ethyl α-hydroxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetate (20.47 g, 90.0%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-3b5926f113534c47a8ec7ba796a20aec
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

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