Benzyl Bromide → HCID 21224436, compound

HRID 1584367Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[O:17][CH3:18].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][C:3]=1[O:17][CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 5-(4-hydroxy-3-methoxyphenyl)pentanoate (27.92 g), benzyl bromide (20.82 g), potassium carbonate (22.9 g) and N,N-dimethylformamide (DMF) (140 ml) was stirred for 15 hours at 90° C. The reaction mixture was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:6, v/v), was obtained ethyl 5-(4-benzyloxy-3-methoxyphenyl)pentanoate (31.64 g, 84%),

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
washFrom the fraction eluted with ethyl acetate-hexane (1:6, v/v)

Sources & evidence

ORD record: ord-d6d73f8177b94c9588b48ac40578240c
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932601

Reaction notes

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