4-Toluenesulfonyl chloride → HCID 86587033, compound

HRID 398765Notes

Reaction equation

HRID 398765 reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]/[C:11](=[CH2:15])[CH2:12][CH2:13][OH:14])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(N(CC)CC)C.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].CN(C1C=CC=CN=1)C>ClCCl>[CH2:6]([O:5][P:4](/[CH:9]=[CH:10]/[C:11](=[CH2:15])[CH2:12][CH2:13][O:14][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 86587034HCID 86587034, compound

Product 1

HCID 86587033HCID 86587033, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of E-5-hydroxy-3-methylidene-1-pentenyl-phosphonic acid diethyl ester (1.07 g, 4.6 mmol), triethylamine (0.7 ml, 5 mmol), tosylchloride (0.96 g, 5 mmol) and dimethylaminopyridine (0.005 g, 0.04 mmol) in anhydrous and dichloromethane is stirred 4 hours at 20° C., concentrated in vacuo and the title product is obtained by flash chromatography on silica gel (1.55 g, 87%).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bba99e4dd2eb47e9a2b448c5f42a64ff
Source dataset
uspto-grants-1998_10
Patent number
US05817647

Reaction notes

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