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-fb1144f8cdb54433b4a74e71c4543d24

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653079B2