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

HRID 1602996ノート

反応式

HRID 1602996 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 54362841ethyl 2-diazo-2-diethoxyphosphoryl-acetate収率 74.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cf15b7adaf604650885787a4c60f9bfa
出典データセット
uspto-grants-1999_11
特許番号
US05985905

反応ノート

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