p-Toluenesulfonyl azide → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

HRID 1398538Notes

Reaction equation

HRID 1398538 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:10])[CH3:9])(=[O:6])[O:4][CH3:5].[H-].[Na+].CC1C=CC(S([N:23]=[N+:24]=[N-])(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][P:3]([C:7](=[N+:23]=[N-:24])[C:8](=[O:10])[CH3:9])(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 13661p-Toluenesulfonyl azideHCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonate

Product 1

HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2-oxo-propyl)-phosphonic acid dimethyl ester (20 g, 0.12 mol) was dissolved in toluene (500 mL) at 0° C. and NaH (4.8 g, 0.12 mol) was added in portions. After the gas evolution had ceased, a solution of 4-methyl-benzenesulfonyl azide (21.4 g, 1.1 mol) was added drop-wise and the mixture was stirred at room temperature for 16 hr. The mixture was diluted with hexanes, filtered through a pad of celite and rinsed with TMBE. The filtrate was concentrated to afford the title compound (16 g, 70%): 1H NMR (400 MHz, DMSO) delta 2.22 (s, 3H), 3.74 (s, 3H), 3.79 (s, 3H).

Workup

  1. filtrationfiltered through a pad of celite
  2. washrinsed with TMBE
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d5f566a1a33648a58645dce47e15fe0f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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