Ethyl diazoacetate → HCID 118161660, compound

HRID 2203678Notes

Reaction equation

HRID 2203678 reaction equation
[CH2:1]1[C:4]2([CH2:8][CH:7]=[CH:6][CH2:5]2)[CH2:3][O:2]1.[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[O:2]1[CH2:3][C:4]2([CH2:8][CH:7]3[CH:6]([CH:11]3[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5]2)[CH2:1]1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 118161592HCID 118161592, compound

Product 1

HCID 118161660HCID 118161660, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 2-oxaspiro[3.4]oct-6-ene (1.0 g, 9.2 mmol) and copper sulfate (145 mg, 0.907 mmol) in toluene (5 mL) was added a solution of ethyl 2-diazoacetate (2.64 g, 22.7 mmol) in toluene (20 mL) at 100° C. over 16 h. The reaction mixture was concentrated, and the resulting residue was purified by flash column chromatography (10% ethyl acetate in petroleum ether) to afford product as a brown oil (1.5 g, 84% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by flash column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-cd3188752e214fc3acbffb793914acd8
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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