4-Toluenesulfonyl chloride → HCID 57742403, compound

HRID 2041922Notes

Reaction equation

HRID 2041922 reaction equation
[CH2:1]([P:4](=[O:10])([CH2:7][CH2:8][CH3:9])[CH2:5][OH:6])[CH2:2][CH3:3].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>CCOCC>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:6][CH2:5][P:4]([CH2:7][CH2:8][CH3:9])([CH2:1][CH2:2][CH3:3])=[O:10])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18981637HCID 18981637, compound

Product 1

HCID 57742403HCID 57742403, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To dipropyl hydroxymethylphosphine-oxide (Ref. U.S. Pat. No. 5,272,128) (16.4 g, 0.1 mol) in anhydrous ether (200 mL) at 0° C., was added p-toluenesulfonyl chloride (19.1 g, 0.1 mol), triethyl amine (27.8 mL, 0.2 mol). The reaction was stirred at room temperature over night. The ether solution was decanted, and the precipitate was washed in a filter funnel with ˜1 L ether until HPLC found no product. Combined ether layer were concentrated. The crude product was purified on silica gel chromatography with 8% MeOH/DCM.

Workup

  1. customThe ether solution was decanted
  2. washthe precipitate was washed in a filter funnel with ˜1 L ether until HPLC
  3. concentrationCombined ether layer were concentrated
  4. customThe crude product was purified on silica gel chromatography with 8% MeOH/DCM

Sources & evidence

ORD record
ord-6996897338f14d43b4f31a94a84e5bb2
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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