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

HRID 397619

Reaktionsgleichung

Reaktionsgleichung von HRID 397619
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 168478Rhodium acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2dd7fad754604c5fab103b37d6f62d19
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610714B2

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