Chloromethyl Methyl Ether → 1-(Methoxymethyl)-3-methylidenecyclobutane-1-carbonitrile

Temperature

-78 °C

To a mixture of 3-methylenecyclobutanecarbonitrile (1.00 g, 0.0107 mol) in tetrahydrofuran (40 mL, 0.5 mol) was added 2.00 M of lithium diisopropylamide in tetrahydrofuran (6.44 mL) at −78° C. After stirred at −78° C. for 30 min, to the resulting mixture was added chloromethyl methyl ether (1.02 mL, 0.0134 mol). The reaction was stirred at −78° C. for 30 min, then allowed to warm up to rt, quenched with ammonium chloride, then extracted with ether. The combined organic layers were washed with water, brine, dried, and evaporated to dryness. The crude residue was used directly in next step.

1. stirringThe reaction was stirred at −78° C. for 30 min
2. temperatureto warm up to rt
3. customquenched with ammonium chloride
4. extractionextracted with ether
5. washThe combined organic layers were washed with water, brine
6. customdried
7. customevaporated to dryness

ORD record

ord-6e3d1f578ef742da9d5304a0b7f70c9c

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158616B2