Benzyl Bromide → 3-(Benzyloxy)-2-(1-hydroxypropyl)-6-methyl-4H-pyran-4-one
Reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O[CH:20](C1OC(C)=CC(=O)C=1O)[CH2:21]C.C(Br)C1C=CC=CC=1>>[OH:1][CH:2]([C:3]1[O:4][C:5]([CH3:18])=[CH:6][C:7](=[O:17])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:20][CH3:21]Participants
4
Procedure
The title compound was prepared by the method outlined for 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one, using 7.36 g (40 mmol, 1 eq.) of 2-(1-hydroxypropyl)-3-hydroxy-6-methyl-pyran-4(1H)-one and 7.5 g benzyl bromide (44 mmol, 1.1 eq.) to yield the pure product 8.9 g (81.2%) after recrystallisation from CH2Cl2/Pet. ether 40/60, as a white crystalline solid. m.p. 88-89° C.
Sources & evidence
- ORD record
- ord-e075886c1d43470180d253301f1c7daf
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448273B1
Reaction notes
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