Triethylamine → Diisopropyl P-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]phosphonate

HRID 327004Notes

Reaction equation

HRID 327004 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][P:15](=[O:24])([O:20][CH:21]([CH3:23])[CH3:22])[O:16][CH:17]([CH3:19])[CH3:18].C(N(CC)CC)C>CCOCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:13][CH2:14][P:15](=[O:24])([O:16][CH:17]([CH3:19])[CH3:18])[O:20][CH:21]([CH3:23])[CH3:22])(=[O:10])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10867235Diisopropyl hydroxymethylphosphonateHCID 157253702-Chloro-6-methylbenzene-1-sulfonyl chloride

Product 1

HCID 18981636Diisopropyl P-[[(2-chloro-6-methylphenyl)sulfonyloxy]methyl]phosphonateYield 91.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 21.7 g of 2-chloro-6-methylbenzenesulfonyl chloride dissolved in 40 ml of ether was added dropwise over 90 minutes to a mixture of 20.6 g of diisopropyl P-(hydroxymethyl)-phosphonate, (Example 17), 80 ml of ether, and 15.4 ml of triethylamine. The addition was mildly exothermic and the reaction was cooled using a cool water bath (no ice). The reaction was allowed to stir overnight at room temperature and then was diluted with 300 ml of ethyl acetate, washed with three 100 ml portions of water, the organic phase dried with magnesium sulfate, filtered and concentrated under reduced pressure to yield 34.0 g of the desired product as a yellow oil.

Workup

  1. additionThe addition
  2. temperaturethe reaction was cooled
  3. washwashed with three 100 ml portions of water
  4. dry with materialthe organic phase dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-105c062a50c448c68aa14775b0f6893f
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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