Acetic Acid → methyl 3-cyclopropyl-2,3-epoxypropionate

Temperature

-10 °C

A 300-ml three-necked flask equipped with a thermometer and a stirrer was charged with 87 g (0.45 mole) of a 28% sodium methoxide solution in methanol and 21 g (0.30 mole) of cyclopropanecarbaldehyde and, after the contents had been cooled down to −10° C., 48.9 g (0.45 mole) of methyl chloroacetate was added dropwise over 3 hours. After completion of the addition, the reaction mixture was allowed to be warmed up to room temperature and was then stirred at room temperature for 5 hours. Thereafter, 12 g (0.20 mole) of acetic acid was added to neutralize remaining sodium methoxide and the resulting mixture was poured into 140 g of water. The reaction mixture thus obtained was extracted three times each with 50 ml of ethyl acetate and the extracts were washed with 50 ml of saturated salt water. The mixture thus washed was dried over anhydrous sodium sulfate and condensed. The residue was distilled under reduced pressure to yield, as distillates at 70 to 73° C. [6 mmHg (8.0 hPa)], 29.8 g (0.21 mole; yield: 70.0%) of methyl 3-cyclopropyl-2,3-epoxypropionate having the following properties.

1. customA 300-ml three-necked flask equipped with a thermometer and a stirrer
2. additionAfter completion of the addition
3. temperatureto be warmed up to room temperature
4. customThe reaction mixture thus obtained
5. extractionwas extracted three times each with 50 ml of ethyl acetate
6. washthe extracts were washed with 50 ml of saturated salt water
7. washThe mixture thus washed
8. dry with materialwas dried over anhydrous sodium sulfate and condensed
9. distillationThe residue was distilled under reduced pressure

ORD record

ord-6ffdc331deb04eb49930410b3019191e

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07164047B2