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

HRID 606357

Reaktionsgleichung

Reaktionsgleichung von HRID 606357
[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 10 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-4fdc6a81b3a44bec9ff9d7e6a1bd36d1
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915295B2

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