Triethyl phosphonoacetate → 17507-56-1

HRID 1602996Notes

Reaction equation

HRID 1602996 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 5436284117507-56-1Yield 74.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cf15b7adaf604650885787a4c60f9bfa
Source dataset
uspto-grants-1999_11
Patent number
US05985905

Reaction notes

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