Potassium Carbonate → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

HRID 714134Notes

Reaction equation

HRID 714134 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:10])[CH3:9])(=[O:6])[O:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].C(C1C=CC(S([N:38]=[N+:39]=[N-])(=O)=O)=CC=1)CCCCCCCCCCC.[NH4+].[Cl-]>CC#N>[CH3:1][O:2][P:3]([C:7](=[N+:38]=[N-:39])[C:8](=[O:10])[CH3:9])(=[O:6])[O:4][CH3:5]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 109151434-Dodecylbenzenesulfonyl azide

Product 1

HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A suspension of dimethyl(2-oxopropyl)phosphonate (2.1 g, 12.9 mmol) and potassium carbonate (2.2 g, 15.9 mmol) in dry MeCN (40 mL) was treated with slow addition of a solution of 4-dodecylbenzenesulfonyl azide (5.7 g, 16.2 mmol) in dry MeCN (90 mL) for over 30 min. After being stirred for 2.5 h under N2 atmosphere at room temperature, the mixture was treated with saturated NH4Cl (100 mL), poured into a separatory funnel and extracted with EtOAc (3×100 mL), dried over Na2SO4, filtered, solvent evaporated and the residue chromatographed in a cartridge of silicagel (40 g) eluted with 15% to 100% EtOAc in hexane (UV detection at 254 nm), to afford reagent 29 as a light yellow oil.

Workup

  1. additionpoured into a separatory funnel
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customthe residue chromatographed in a cartridge of silicagel (40 g)
  7. washeluted with 15% to 100% EtOAc in hexane (UV detection at 254 nm)

Sources & evidence

ORD record
ord-c06b68e3e3464224a778479bef3ea25f
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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