Reaktion #47087

ord-7777b2e233d64c81ae3edec4c6319a78

Reaktionsgleichung

CC(C)O
2-propanol
CCOC(=O)C=[N+]=[N-]
ethyl diazoacetate
CCOC(=O)COC(C)C
product 405
Ausbeute 51.3%
CCOC(=O)COC(C)C
Isopropoxyacetic acid ethyl ester
Ausbeute 51.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction mixture is filtered through Celite
  2. 2
    Sonstigethe filtrate is evaporated
  3. 3
    workup.DISTILLATIONdistilled at 150° C.

Vorschrift

To a solution of 2-propanol (0.776 mL, 10.0 mmol) in dichloromethane (33 mL) is added rhodium (II) acetate dimer (22 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 750 mg of the product 405. 1H NMR (CDCl3) δ 4.21 (q, 2 H), 4.06 (s, 2 H), 3.73 (m, 1 H), 1.29 (t, 3 H), 1.22 (s, 3 H), 1.19 (s, 3 H); MS: m/z 147 (M++1).

Quelle

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