Cyclopropanecarboxaldehyde → trans-N-methyl-N-methoxy-3-cyclopropylpropenamide

Temperature

-78 °C

To a solution of N-methoxy-N-methyl diethylphosphonoacetamide (34.56 g, 144.5 mmol) in THF (200 mls) at -78° C., was added n-butyllithium (57.8 mls of a 2.5M solution in hexanes, 144.5 mmol) dropwise. Upon completion of addition, the mixture was stirred for 30 mins at -78° C. A solution of cyclopropanecarboxaldehyde (6.75 g, 96.3 mmol) in THF (50 mls) was then added dropwise. Upon completion of addition, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NH4Cl (200 mls) and the THF was stripped off in vacuo. The aqueous residue was extracted with ethylacetate (3×200 mls). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was chromatographed (silica gel, ether:hexanes, 3:2) to afford 14.09 g (94%) of trans-N-methyl-N-methoxy-3-cyclopropylpropenamide as a colorless oil.

1. additionUpon completion of addition
2. additionUpon completion of addition
3. customthe cooling bath was withdrawn
4. temperatureto warm to r.t
5. additionIt was then diluted with aqueous sat'd NH4Cl (200 mls)
6. extractionThe aqueous residue was extracted with ethylacetate (3×200 mls)
7. dry with materialdried with MgSO4
8. concentrationconcentrated
9. customThe resulting residue was chromatographed (silica gel, ether:hexanes, 3:2)

ORD record

ord-e7c14a57a20044edab54869ee8b15d7d

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05559144