Ethyl diazoacetate → ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate

HRID 397619

Reaction equation

HRID 397619 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH2:9][CH2:10]2)=[CH:5][CH:4]=1.[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[CH:7]1[CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]1[CH2:9][CH2:10]2

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 5947787-Methoxy-1,2-dihydronaphthalene

Product 1

HCID 23001093ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

7-Methoxy-1,2-dihydronaphthalene (8.8 g, 0.055 mol) was mixed with 1 ml of degassed absolute methylene chloride and 20 mg of rhodium acetate (appr. 0.1 mol %). The reaction mixture was bubbled with nitrogen and ethyl diazoacetate (2 eq, 50% solution in degassed abs. methylene chloride) was added slowly through the syringe (flow rate about 1 ml/hour) to the stirred solution at ambient temperature. Gas evolution started upon the addition. The reaction was monitored by GC. Additional amount of catalyst was added during the reaction (about 20 mg). GC-ratio of cis/trans isomers was 21:48.

Workup

  1. additionwas added slowly through the syringe (flow rate about 1 ml/hour) to the stirred solution at ambient temperature
  2. additionGas evolution started upon the addition
  3. additionAdditional amount of catalyst was added during the reaction (about 20 mg)

Sources & evidence

ORD record
ord-2dd7fad754604c5fab103b37d6f62d19
Source dataset
uspto-grants-2003_08
Patent number
US06610714B2

Linked notes

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