Diazomethane → HCID 54330669, compound

HRID 1586902Notes

Reaction equation

HRID 1586902 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:15][CH:14]=[CH:13][CH2:12][C@@H:11]1[C:16]([OH:18])=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:21])=[N-]>CCOCC>[C:1]([O:9][C@H:10]1[CH2:15][CH:14]=[CH:13][CH2:12][C@H:11]1[C:16]([O:18][CH3:21])=[O:17])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 14484454HCID 14484454, compound

Product 1

HCID 54330669HCID 54330669, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-benzoyloxycyclohex-4-ene-2-carboxylic acid (5, 160 mg, 0.645 mmol) in ether (5 ml) is treated with a solution of diazomethane (excess) in ether. The solvent was removed under vacuum to yield methyl cis-2-benzoyloxy-cyclohex-4-enecarboxylate (6, 168 mg, 100%) as a colorless oil. When enantiomerically pure starting material was used, the product of this reaction was >97% enantiomerically pure. [α]D (c 6.35, acetone)=-89.5 for the 1S,2R isomer).

Workup

  1. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-22fe9205315a45869da6548137814bc3
Source dataset
uspto-grants-1993_06
Patent number
US05216141

Reaction notes

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