Diethyl Ether → HCID 54330336, compound

HRID 485714Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]1([CH3:21])[C@H:9]([CH:10]=[C:11](Br)Br)[C@H:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCOCC.P(O)(O)([O-])=O.[Na+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1([CH3:21])[C@H:9]([C:10]#[CH:11])[C@H:8]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

Conditions

Temperature: -80 °C

Procedure

47 ml of a solution of 2.34M of butyllithium in hexane were slowly added at -100° C. to a solution of 38.7 g of tert.-butyl (1R,trans) 2,2-dimethyl-3-(2,2-dibromovinyl)-cyclopropane-carboxylate, 200 ml of ether and 200 ml of tetrahydrofuran and the mixture was stirred for 90 minutes at -80° C. and was poured into 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 under reduced pressure to obtain 9.3 g of tert.-butyl (1R,trans) 2,2-dimethyl-3-ethynyl-cyclopropane-carboxylate with a boiling point of 30° C. at 0.1 mm Hg.

Workup

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

Sources & evidence

ORD record: ord-84e1259cdd434735bcd1fd88909a41fe
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537897

Reaction notes

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