Diethyl Ether → Diisopropyl P-[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphonate

HRID 327005Notes

Reaction equation

HRID 327005 reaction equation
CCOCC.[OH:6][CH2:7][P:8](=[O:17])([O:13][CH:14]([CH3:16])[CH3:15])[O:9][CH:10]([CH3:12])[CH3:11].C(N(CC)CC)C.[F:25][C:26]([F:38])([F:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34]>C(OCC)(=O)C>[F:38][C:26]([F:25])([F:37])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33]([O:6][CH2:7][P:8](=[O:17])([O:9][CH:10]([CH3:12])[CH3:11])[O:13][CH:14]([CH3:16])[CH3:15])(=[O:34])=[O:35]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 10867235Diisopropyl hydroxymethylphosphonate

Product 1

HCID 18981640Diisopropyl P-[[(2-(trifluoromethyl)phenyl)sulfonyloxy]methyl]phosphonateYield 64.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 30 ml of ether, 13.3 g of diisopropyl P-(hydroxymethyl)phosphonate, prepared in Example 17, and 10.5 ml of triethylamine was added dropwise over 60 minutes to a solution of 15.35 g of 2-(trifluoromethyl)benzenesulfonyl chloride and 50 ml of ether. After the mild exotherm, the reaction was allowed to stir at room temperature overnight and then was diluted with 200 ml of ethyl acetate, the ethyl acetate solution washed with two 100 ml portions of water, dried with magnesium sulfate, filtered, and concentrated to yield 16.3 g of the desired product as an oil.

Workup

  1. washthe ethyl acetate solution washed with two 100 ml portions of water
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c897cd172b4a4cbea2f1a89c5fc5d7dc
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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