Methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate → HCID 45090112, compound

HRID 485712Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]1([CH3:18])[C@@H:9]([CH:10]=[C:11](Br)Br)[C@H:8]1[C:14]([O:16][CH3:17])=[O:15].P(O)(O)([O-])=O.[Na+]>C1CCCCC1>[CH3:6][C:7]1([CH3:18])[C@@H:9]([C:10]#[CH:11])[C@H:8]1[C:14]([O:16][CH3:17])=[O:15]

Participants

Conditions

Temperature: -60 °C

Procedure

100 ml of a solution of 1.85M of butyllithium in cyclohexane were slowly added at -100° C. to a cyclohexane solution containing 58.34 g of methyl (1R,cis) 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-carboxylate and the mixture was stirred at -100° C. for 30 minutes, at -60° C. for one hour and was then poured into an iced aqueous monosodium phosphate solution. The mixture was extracted with benzene and the organic phase was evaporated to dryness under reduced pressure. The residue was rectified to obtain 14.5 g of methyl (1R,cis) 2,2-dimethyl-3-ethynyl-cyclopropane-carboxylate with a boiling point of 40° C. at 0.5 mm Hg.

Workup

extractionThe mixture was extracted with benzene
customthe organic phase was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-0e00f13adc70420d8dc98f0cff1f9715
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537897

Reaction notes

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