3-[5-Hydroxy-2-(4-hydroxy-phenyl)benzofuran-7-yl]-acrylic acid methyl ester → 3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]=[CH:5][C:6]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:9]=[C:8]([OH:22])[CH:7]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:9]=[C:8]([OH:22])[CH:7]=1Participants
Procedure
To a solution of 3-[5-hydroxy-2-(4-hydroxy-phenyl)benzofuran-7-yl]-acrylic acid methyl ester 59 (0.1 g, 0.32 mmol) in methanol (5 mL) and purged with nitrogen was added catalytic 10% palladium on carbon. The reaction vessel was evacuated and a balloon of hydrogen was added. After 7 hours, the reaction was filtered and the solvent removed in vacuo. The product was purified via flash chromatography on silica gel, eluting with 7% methanol in dichloromethane to give 0.015 g of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionic acid methyl ester 60: Mp=167–170° C.; 1H NMR (DMSO-d6) δ 9.83 (s, 1 H), 9.08 (s, 1 H), 7.70 (d, 2 H, J=8.6 Hz), 7.00 (s, 1 H), 6.87 (d, 2 H, J=8.6 Hz), 6.73 (d, 1 H, J=2.3 Hz), 6.53 (d, 1 H, J=2.2 Hz), 3.59 (s, 3 H), 3.07 (t, 2 H, J=7.5 Hz), 2.77 (t, 2 H, J=7.6 Hz); MS 313 (M+H)+.
Workup
- customThe reaction vessel was evacuated
- additiona balloon of hydrogen was added
- filtrationthe reaction was filtered
- customthe solvent removed in vacuo
- customThe product was purified via flash chromatography on silica gel
- washeluting with 7% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-39f8bc6aa9184207aa3bf36a57a6b7db
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022733B2
Reaction notes
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