Water → (+/-)-N-Methoxy-N-methyl-2-(prop-2-en-1-yloxy)propanamide

Temperature

0 °C

A suspension of N-methyl-O-methyl hydroxylamine hydrochloride (10.0 g, 104 mmol, 2 equiv) in dichloromethane (100 mL) was treated with trimethylaluminum (52.0 mL, 104 mmol, 2 equiv) at 0° C. After stirring for 1 hour at 0° C., a dichloromethane (50 mL) solution of (±)-methyl 2-(prop-2-en-1-yloxy)propanoate (7.50 g, 52.0 mmol) was added over 15 minutes. The mixture was warmed to ambient temperature and stirred for an additional 14 hours. The mixture was treated with water (500 mL) and extracted with dichloromethane (2×300 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo to provide the titled compound.

1. temperatureThe mixture was warmed to ambient temperature
2. stirringstirred for an additional 14 hours
3. extractionextracted with dichloromethane (2×300 mL)
4. dry with materialThe combined organic extracts were dried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-c4780dd9a55b40a7b011677e99a0cc97

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486946B2