Ethyl diazoacetate → 4-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

HRID 16227

Reaktionsgleichung

Reaktionsgleichung von HRID 16227
[C:1]([Si:5]([O:18][CH:19]1[CH2:25][CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[N-]>ClCCl>[CH2:32]([O:31][C:29]([CH:28]1[CH:22]2[CH:23]1[CH2:24][CH2:25][CH:19]([O:18][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:20][CH2:21]2)=[O:30])[CH3:33]

Komponenten

4

Edukt 2

HCID 12192Ethyl diazoacetateHCID 67512396Tert-butyl-(cyclohept-4-enyloxy)-diphenyl-silane

Produkt 1

HCID 686886034-(Tert-butyl-diphenyl-silanyloxy)-bicyclo[5.1.0]octane-8-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of Example 8C (2.2 g, 6.28 mmoles) and Rh2(OAc)4 (2 mg, 4.3 μmol) in dichloromethane (2 mL), ethyl diazoacetate (0.717 g, 6.28 mmoles) in dichloromethane (4 mL) was added over two hours via a syringe pump. The solvent was evaporated in vacuo and product purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20) to provide the title compound.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo and product
  2. custompurified by flash column chromatography (hexanes:ethyl acetate 100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-e40caf334b0742ffaf4ef4909375fc79
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737137B2

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