Ethyl diazoacetate → HCID 86720189, compound

HRID 928096Notes

Reaction equation

HRID 928096 reaction equation
[N+](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-].[CH:9]1([C:14](=[O:16])[CH3:15])[CH2:13][CH:12]=[CH:11][CH2:10]1>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:14]([CH:9]1[CH2:13][CH:12]2[CH:11]([CH:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:10]1)(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 14890212HCID 14890212, compound

Product 1

HCID 86720189HCID 86720189, compound

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl diazoacetate (0.266 mL, 2.179 mmol) in dichloromethane (6 mL) was added over 6 hours via syringe pump to a solution of 1-(cyclopent-3-en-1-yl)ethanone (200 mg, 1.816 mmol) and rhodium(II) acetate dimer (16.1 mg, 0.036 mmol) in dichloromethane (6 mL). After an additional 11 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (10-30% ethyl acetate/hexanes) to afford ethyl 3-acetylbicyclo[3.1.0]hexane-6-carboxylate. MS ESI calc'd. for C11H17O3 [M+H]+ 197. found 197.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (10-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ab597d2c11a440148ac971d2a3f2a84b
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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