Triethylamine → O-Ethyl P-methyl[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphinate

HRID 327010Notes

Reaction equation

HRID 327010 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:21])([F:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17].[CH3:22][P:23]([CH2:28][OH:29])(=[O:27])[O:24][CH2:25][CH3:26]>C1COCC1>[CH3:22][P:23]([CH2:28][O:29][S:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([F:8])([F:20])[F:21])(=[O:18])=[O:17])(=[O:27])[O:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 13923056O-ethyl P-methyl(hydroxymethyl)phosphinate

Product 1

HCID 18981657O-Ethyl P-methyl[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphinateYield 14.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8 ml of triethylamine diluted with 25 ml of THF was slowly added dropwise over two hours to a mixture of 11.2 g of 2-(trifluoromethyl)benzenesulfonyl chloride, 6.05 g of O-ethyl P-methyl(hydroxymethyl)phosphinate, (Example 22, Method B), and 60 ml of THF. A white precipitate began to form shortly after the addition of the triethylamine solution was begun. No significant exotherm occurred and the reaction was allowed to stir overnight. The reaction mixture was concentrated and the concentrate was partitioned between 220 ml of ethyl acetate and 50 ml of water. The organic phase was washed with an additional 50 ml of water, dried with magnesium sulfate, gravity filtered, and concentrated to yield an orange solid. The solid was flash chromatographed on silica gel using ethyl acetate to yield 2.2 g of the desired product, melting point 91°-92.5° C.

Workup

  1. customto form shortly
  2. concentrationThe reaction mixture was concentrated
  3. customthe concentrate was partitioned between 220 ml of ethyl acetate and 50 ml of water
  4. washThe organic phase was washed with an additional 50 ml of water
  5. dry with materialdried with magnesium sulfate, gravity
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an orange solid
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-623da70bd1374f4db55962d2acd72a6b
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

Loading…