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

HRID 1602996노트

반응식

HRID 1602996 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 54362841ethyl 2-diazo-2-diethoxyphosphoryl-acetate수율 74.5%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cf15b7adaf604650885787a4c60f9bfa
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05985905

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