Triethyl phosphonoacetate → ethyl 2-diazo-2-diethoxyphosphoryl-acetate

HRID 1602996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602996
CC(C)([O-])C.[K+].[CH3:7][CH2:8][O:9][C:10]([CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])=[O:11].C1C2C(=CC=CC=2)C=CC=1S([N:34]=[N+:35]=[N-])(=O)=O>C1(C)C=CC=CC=1>[N+:34](=[C:12]([P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])[C:10]([O:9][CH2:8][CH3:7])=[O:11])=[N-:35]

Komponenten

5

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 109773552-Naphthalenesulfonyl azideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 54362841ethyl 2-diazo-2-diethoxyphosphoryl-acetateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A suspension of potassium t-butoxide (4.42 g, 39.4 mmol) in toluene (200 ml) was stirred at 0° under Ar for 10 minutes. A solution of ethyl diethoxyphosphoryl acetate (6.53 ml, 32.9 mmol) in toluene (20 ml) was added in 20 minutes keeping the temperature below 5°. Another solution of 2-naphthalenesulfonyl azide (7.67 g, 32.9 mmol) was added dropwise below 5°, and the reaction mixture was warmed to RT and stirred overnight. The resulting suspension was filtered and the filtrate washed with toluene. The pooled organic phase was concentrated and the brown oily residue distilled producing pure title compound (6.12 g, 24.5 mmol, yield 74.3%) as a yellow oil, b.p.=70-73°/0.02 mmHg.

Aufarbeitung

  1. customthe temperature below 5°
  2. stirringstirred overnight
  3. filtrationThe resulting suspension was filtered
  4. washthe filtrate washed with toluene
  5. concentrationThe pooled organic phase was concentrated
  6. distillationthe brown oily residue distilled

Quellen und Nachweise

ORD-Eintrag
ord-cf15b7adaf604650885787a4c60f9bfa
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985905

Notizen zur Reaktion

Wird geladen…