4-Toluenesulfonyl chloride → 2-Benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propane

HRID 266231Notes

Reaction equation

HRID 266231 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH:10]([CH2:13][O:14][CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][O:12][S:37]([C:34]1[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)(=[O:39])=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 537262552-Benzyloxymethyl-3-diethylphosphonomethoxy-1-propanol

Product 1

HCID 544722702-Benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propaneYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2-benzyloxymethyl-3-diethylphosphonomethoxy-1-propanol (0.25 g, 0.72 mmol) in 5 mL of CH2Cl2 was cooled to 0° C. and treated with triethylamine (0.22 g, 2.16 mmol). A solution of p-toluenesulfonyl chloride (0.151 g, 0.79 mmol) in 2 mL of CH2Cl2 was added next and the reaction mixture allowed to warm gradually to room temperature. After 14 hours at room temperature, the mixture was diluted with CH2Cl2 and washed with two portions of 10% aqueous HCl and saturated sodium chloride solution, dried over MgSO4, filtered, and concentrated to give an orange oil. Purification by column chromatography on silica gel (1-3% ethanol in ethyl acetate) provided 0.295 g of 2-benzyloxymethyl-3-diethylphosphonomethoxy-1-(p-toluenesulfonyloxy)propane as a pale yellow oil.

Workup

  1. washwashed with two portions of 10% aqueous HCl and saturated sodium chloride solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an orange oil
  6. customPurification by column chromatography on silica gel (1-3% ethanol in ethyl acetate)

Sources & evidence

ORD record
ord-c79a50b82dcf45c2930754bc3992feaa
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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