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

HRID 397619

反応式

HRID 397619 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 168478Rhodium acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2dd7fad754604c5fab103b37d6f62d19
出典データセット
uspto-grants-2003_08
特許番号
US06610714B2

関連ノート

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