Methyl Acrylate → HCID 1474745, Verbindung

Temperatur

100 °C

A mixture of (4-bromophenyl)-(cyclopropyl)methanone (0.450 g, 2.00 mmol), palladium acetate 49 mg, 0.220 mmol), triphenylphosphine (55 mg, 0.21 mmol), methyl acrylate (0.43 g, 2.50 mmol) and triethylamine (10 ml, 72 mmol) was heated to 100° C. for 48 in a closed reaction vial. The reaction mixture was cooled to room temperature. The solid was removed by filtration. A mixture of ice and 1 N hydrochloric acid was added to the liquid. The mixture was stirred for 1 h at room temperature. It was extracted with ethyl acetate (2×150 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g) using a mixture of dichloromethane/ethyl acetate/heptane (1:1:1) as eluent, to give 217 mg of (E)-3-(4-(cyclopropanecarbonyl)phenyl)acrylic acid methyl ester.

1. temperatureThe reaction mixture was cooled to room temperature
2. customThe solid was removed by filtration
3. additionA mixture of ice and 1 N hydrochloric acid
4. additionwas added to the liquid
5. extractionIt was extracted with ethyl acetate (2×150 ml)
6. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml)
7. dry with materialdried over magnesium sulphate
8. customThe solvent was removed in vacuo
9. customThe crude product was purified by flash chromatography on silica (40 g)
10. additiona mixture of dichloromethane/ethyl acetate/heptane (1:1:1) as eluent

ORD-Eintrag

ord-e2aac1089cfd45189cd6646ce92bc719

Quelldatensatz

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07101898B2