Benzyl Bromide → 2-(Hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

HRID 1634599Notes

Reaction equation

HRID 1634599 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5](C)=[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.OCC1OC=CC(=O)C=1O.C(Br)C1C=CC=CC=1>>[OH:1][CH2:2][C:3]1[O:4][CH:5]=[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

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 98696223-hydroxy-2-(hydroxymethyl)-4H-pyran-4-oneHCID 111394092-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one

Product 1

HCID 217925452-(Hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

Procedure

The title compound was prepared by the method outlined for 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1H)-one, using 7.1 g (50 mmol, 1 eq.) of 2-hydroxymethyl-3-hydroxy-pyran-4(1 H)-one and 9.5 g benzyl bromide (55 mmol, 1.1 eq.) to yield the crude product as an organe oil. Further purification by column chromatography on silica gel (eluant: 10% CH3OH/90% CHCl3) furnished the pure product (9.4 g, 81%) as a bright yellow oil. (Looker and Clifton (1986).

Workup

  1. customto yield the crude product as an organe oil

Sources & evidence

ORD record
ord-a4e7add9c8954a579ae3de5dab5b1bae
Source dataset
uspto-grants-2003_01
Patent number
US06506911B2

Reaction notes

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