Methyl chloroformate → Methyl hept-6-en-2-ynoate

A solution of allylmagnesium bromide (1M, 150 mL, 150 mmol) in ether under a nitrogen atmosphere was cooled to −10° C., and propargyl chloride (5.4 mL, 75 mmol) was added dropwise. The solution was stirred for 24 h at room temperature, and then cooled to 0° C. Methyl chloroformate was added dropwise, and the solution was allowed to stir at room temperature for 4 h. The reaction was quenched by cautious addition of satd aq NH4Cl (100 mL) at 0° C. The organic layer was washed with brine, dried, and evaporated to a residue. Chromatography on silica gel provided the title compound (4.5 g, 44%) as a pale yellow liquid.

1. temperaturecooled to 0° C
2. stirringto stir at room temperature for 4 h
3. customThe reaction was quenched by cautious addition of satd aq NH4Cl (100 mL) at 0° C
4. washThe organic layer was washed with brine
5. customdried
6. customevaporated to a residue

ORD record

ord-71784f9d46fc4fe59851ac6dc36d3d40

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039465B2