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

HRID 1634602Notes

Reaction equation

HRID 1634602 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[O:5][C:6]([CH3:19])=[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(C)=CC(=O)C=1OCC1C=CC=CC=1)[CH2:22]C>>[CH3:1][O:2][CH:3]([C:4]1[O:5][C:6]([CH3:19])=[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)[CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 117473362-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-oneHCID 186788263-(Benzyloxy)-2-(1-hydroxypropyl)-6-methyl-4H-pyran-4-one

Product 1

HCID 186788002-(1-methoxypropyl)-3-benzyloxy-6-methyl-pyran-4(1H)-oneYield 90.3%

Procedure

In an analogous procedure in the preparation of 2-methoxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one using 2-(1-hydroxypropyl)-3-benzyloxy-6-methyl-pyran-4(1H)-one (5.48 g, 20 mmol, 1 eq.) yielded the title compound (5.2 g, 90.3%) as an orange oil which solidified on cooling. Recrystallisation from CH2Cl2/Pet. ether 40/60 afforded the pure product as a white crystalline solid. m.p. 63-65° C.

Sources & evidence

ORD record
ord-a459e845e96a48cb81170022509257b1
Source dataset
uspto-grants-2003_01
Patent number
US06506911B2

Reaction notes

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