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

Temperature

-78 °C

To a solution of N-methoxy-N-methyl diethylphosphonoacetarnide (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 Upon completion of addition, the cooling bath was withdrawn and the reaction allowed to warm to r.t. It was then diluted with aqueous sat'd NH4Cl (200 mls) and the THF was stripped off in vacuo.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-cyclopropylpropenarnide 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 customthe cooling bath was withdrawn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-aeb5041538934a6eae40cf86c3b49508

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05476873