Benzyl Bromide → 3-(4-Benzyloxy-2-formyl-phenyl)-acrylic acid tert-butyl ester

HRID 1181102Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(2-formyl-4-hydroxy-phenyl)-acrylic acid tert-butyl ester (4.97 g, 20.0 mmol) in DMF (40 mL) was added benzyl bromide (2.85 mL, 24.0 mmol) and Cs2CO3 (7.82 g, 24.0 mmol). The suspension was stirred at 80° C. for 30 min, and TLC indicated the reaction was complete. The mixture was quenched with H2O (500 mL) and extracted with EtOAc (2×100 mL). The combined organics were dried (Na2SO4) and concentrated to a residue, which was purified by silica gel chromatography (hexanes/EtOAc 9/1) to afford the title compound as yellow solid (6.70 g, 99%).

Workup

customThe mixture was quenched with H2O (500 mL)
extractionextracted with EtOAc (2×100 mL)
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated to a residue, which
customwas purified by silica gel chromatography (hexanes/EtOAc 9/1)

Sources & evidence

ORD record: ord-876bc0b865b441609947967e0aa6bb7f
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

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