Ethanol → tert.butyl (1R, cis)2,2-dimethyl-3-(ethoxycarbonyl-ethynyl)-cyclopropane-carboxylate

HRID 464448Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(Cl)Cl.[CH2:21](O)[CH3:22]>CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([O:9][CH2:21][CH3:22])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

Conditions

Temperature: 20 °C

Procedure

4 g of the product of Step A, 3.4 g of dicyclohexylcarbodiiumide and 6 mg of 4-dimethylamino-pyridine were added to 30 ml of methylene chloride followed by the addition of 1.5 ml of ethanol and the mixture was stirred at 20° C. for 16 hours. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 4.25 g of tert.butyl (1R, cis)2,2-dimethyl-3-(ethoxycarbonyl-ethynyl)-cyclopropane-carboxylate.

Workup

filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-1964adb1ef5042999cdebe9fe9bc7068
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04547522

Reaction notes

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