Hydrochloric Acid → [Rac]-3-(4-benzyloxy-benzofuran-7-yl)-2-ethoxy-propionic acid methyl ester

HRID 479196Notes

Reaction equation

[Mg].[CH2:2]([O:4][C:5](=[O:28])/[C:6](/[O:25][CH2:26][CH3:27])=[CH:7]/[C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[C:11]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:9]=1)C.[H][H].Cl>CO.C1COCC1>[CH3:2][O:4][C:5](=[O:28])[CH:6]([O:25][CH2:26][CH3:27])[CH2:7][C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[C:11]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Magnesium turnings (0.5 g, 20.6 mmol) were added to a stirred solution of 3-(4-benzyloxy-benzofuran-7-yl)-2Z-ethoxy-acrylic acid ethyl ester (0.8 g, 2.18 mmol) in methanol (26 ml) and THF (13 ml) at ambient temperature. The suspension was warmed to 40° C. until evolution of hydrogen commenced. Then, the heating bath was replaced by a water bath, additional magnesium turnings (1 g, 41.2 mmol) were added and stirring of the reaction mixture was continued for 12 h. The suspension was cooled to 0° C., then 25% aqueous hydrochloric acid was added till all the solid had dissolved. The mixture was extracted twice with ethyl acetate and the combined ethyl acetate solutions were washed three times with water and dried over sodium sulfate. The solvent was evaporated to afford the title compound (0.77 g, 2.16 mmol, 99%) which was used in the next stage without further purification.

Workup

customThen, the heating bath was replaced by a water bath
dissolutionhad dissolved
extractionThe mixture was extracted twice with ethyl acetate
washthe combined ethyl acetate solutions were washed three times with water
dry with materialdried over sodium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-df8cf065d30c4d2889d665dfe071e82b
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

Loading…