HCID 15735543, compound → HCID 15735657, compound

HRID 704608Notes

Reaction equation

HRID 704608 reaction equation
[CH:1]1(/[CH:7]=[C:8](\[CH2:14][P:15]([O:21]CC)([CH2:17][CH:18]([CH3:20])[CH3:19])=[O:16])/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)Cl.CO.C(O)(=O)C>Cl.C(OCCCC)(=O)C>[CH:1]1(/[CH:7]=[C:8](\[CH2:14][P:15]([OH:21])([CH2:17][CH:18]([CH3:20])[CH3:19])=[O:16])/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 15735543HCID 15735543, compoundHCID 21866353chloroform methanol HOAc

Product 1

HCID 15735657HCID 15735657, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 20072624HCID 20072624, compoundSolvent

Procedure

A solution of 107 mg (0.31 millimole) of ethyl (Z)-3-cyclohexyl-2-(ethoxyisobutylphosphinoyl)methylpropenoate in 1.0 ml of 4N HCl-butyl acetate was heated in a sealed tube at 100° C for 2 hours. After cooling, the solvent was evaporated under reduced pressure, and the residue was purified by "dry-column" flash chromatography 15 g of silica gel 60 made by E. Merck & Co.; chloroform-methanol-acetic acid (50:1:1)] to give 91 mg (yield 94%) of the captioned compound as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by "dry-column" flash chromatography 15 g of silica gel 60

Sources & evidence

ORD record
ord-6730d607e7f34f129051f00d74dbd838
Source dataset
uspto-grants-1991_01
Patent number
US04988681

Reaction notes

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