Diethyl Ether → HCID 18981688, compound

HRID 327003Notes

Reaction equation

HRID 327003 reaction equation
[OH:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].C(N(CC)CC)C.CCOCC.[F:23][C:24]([F:36])([F:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32]>C(OCC)(=O)C>[F:36][C:24]([F:23])([F:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([O:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])(=[O:32])=[O:33]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8471TriethylamineHCID 76513Diethyl phosphonomethanolHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 18981688HCID 18981688, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 11.1 g of diethyl P-(hydroxymethyl)phosphonate (Example 17), 11 ml of triethylamine and 30 ml of ether was added dropwise over one hour to 15.5 g of 2-(trifluoromethyl)benzenesulfonyl chloride and 50 ml of anhydrous ether. The addition was mildly exothermic and a white precipitate began to form shortly after the addition was begun. The reaction was stirred overnight, then diluted with 300 ml of ethyl acetate and washed with three 85 ml portions of water. The organic phase was dried with magnesium sulfate, filtered and concentrated. The resulting crude product was purified via flash chromatography on Merck® silica gel (230-400 mesh) eluting with hexanes and ethyl acetate to yield 10.5 g of the desired product as an oil.

Workup

  1. additionThe addition
  2. customto form shortly
  3. additionafter the addition
  4. washwashed with three 85 ml portions of water
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified via flash chromatography on Merck® silica gel (230-400 mesh)
  9. washeluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-25eb6add738e4b73a0450e97013ee15a
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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