Reaktion #47088

ord-1a5b12cd52534597acd79291a1c1607a

Reaktionsgleichung

OC1CCCCC1
cyclohexanol
CCOC(=O)C=[N+]=[N-]
ethyl diazoacetate
CCOC(=O)COC1CCCCC1
product 407
CCOC(=O)COC1CCCCC1
Cyclohexyloxyacetic acid ethyl ester

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered through Celite
  2. 2
    Sonstigethe filtrate is evaporated
  3. 3
    workup.DISTILLATIONdistilled at 150° C.

Vorschrift

To a solution of cyclohexanol (1.0 g, 0.95 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (44 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is diluted with Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.57 g of the product 407. 1H NMR (CDCl3) δ 4.23 (q, 2H), 4.10 (s, 2H), 3.33 (m, 1H), 1.93 (m, 2H), 1.74 (m, 2H), 1.54 (m, 1H), 1.4-1.1 (m, 8H)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741493B2uspto-grants-2010_06