Benzyl Bromide → 3-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

HRID 1268959Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-(4-hydroxyphenyl)lactate (22.4 g) in N,N-dimethylformamide (220 ml) were added benzyl bromide (21.9 g) and calcium carbonate (35.3 g), and the reaction mixture was stirred at 50° C. for 2 hours. The reaction solution was partitioned between ethyl acetate and water, and then the separated ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=7/3) to give the target compound (31.0 g) as a pale yellow oil.

Workup

customThe reaction solution was partitioned between ethyl acetate and water
dry with materialthe separated ethyl acetate layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column (eluant; hexane/ethyl acetate=7/3)

Sources & evidence

ORD record: ord-d983d3ae841643adabe422833a8c596f
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199139B2

Reaction notes

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