2-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one → 2-(1-Methoxyethyl)-3-benzyloxy-pyran-4(1H)-one

HRID 1249792Notes

Reaction equation

HRID 1249792 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:5][C:6](C)=[CH:7][C:8](=[O:18])[C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O[CH:21](C1OC=CC(=O)C=1OCC1C=CC=CC=1)C>>[CH3:1][O:2][CH:3]([C:4]1[O:5][CH:6]=[CH:7][C:8](=[O:18])[C:9]=1[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:21]

Participants

3

Reactant 2

HCID 117473362-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-oneHCID 186788152-(1-hydroxyethyl)-3-benzyloxy-pyran-4(1H)-one

Product 1

HCID 186788162-(1-Methoxyethyl)-3-benzyloxy-pyran-4(1H)-oneYield 92.3%

Procedure

In an analogous procedure in the preparation of 2-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one using 2-(1-hydroxyethyl)-3-benzyloxy-pyran-4(1H)-one (2.46 g, 10 mmol, 1 eq.) yielded the title compound as a yellow oil (2.4 g, 92.3%). Further purification by column chromatography on silica gel (eluant: EtOAc) furnished the pure product (2.1 g, 80.8%) as a bright yellow oil.

Sources & evidence

ORD record
ord-7e629257e4274a80acdaf3905b05f33d
Source dataset
uspto-grants-2002_01
Patent number
US06335353B1

Reaction notes

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