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

HRID 1038039Notes

Reaction equation

HRID 1038039 reaction equation
[H-].[Na+].[CH3:3][O:4][P:5]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[O:6][CH3:7].S([N:23]=[N+:24]=[N-])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[CH3:3][O:4][P:5]([C:9](=[N+:23]=[N-:24])[C:10](=[O:12])[CH3:11])(=[O:8])[O:6][CH3:7]

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 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60% in mineral oil, 0.83 g, 20.8 mmols) in THF (50 ml) was added dropwise at 0 C (2-oxo-propyl)-phosphonic acid dimethyl ester (3.1 g, 18.7 mmols) in THF (50 ml), and the solution was stirred at 0 C for one hour. Tosyl azide (4 g, 20 mmols) was added in one portion, stirred at 0 C for 10 minutes, filtered through Celite and concentrated. The residue was purified by column chromatography on silica gel using ethyl acetate to yield the title compound (2.9 g, 81%) as oil. (Eur. J. Org. Chem. 2003, 821-832.)

Workup

  1. stirringstirred at 0 C for 10 minutes
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c152960a339d4143bcfa1de460612382
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…