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

HRID 428000Notes

Reaction equation

[CH3:1]I.[OH:3][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[H-].[Na+].O>CN(C)C=O>[CH3:1][O:3][CH:4]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl iodide (20.25 g, 143 mmol) was added to a solution of ethyl α-hydroxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetate (14.00 g, 47.6 mmol) in N,N-dimethylformamide (40 ml), and the mixture was stirred at 0° C. 60% oily sodium hydride (1.90 g, 47.5 mmol) was added thereto. After 30 minutes, water (100 ml) was added, and the mixture was extracted with ether 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-methoxy-2-(tetrahydropyran-2-yloxymethyl)phenylacetate (14.00 g, 95.5%) as an oil.

Workup

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

Sources & evidence

ORD record: ord-406c2142f4254b1dac7c5304edb29bd7
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313150B1

Reaction notes

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