1-Octyne → HCID 10857821, compound

HRID 1873089Notes

Reaction equation

HRID 1873089 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].COP([O-])OC.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44]=[C:45]([P:52](=[O:59])([O:56][CH2:57][CH3:58])[O:53][CH2:54][CH3:55])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:44]=[C:45]([P:52](=[O:59])([O:56][CH2:57][CH3:58])[O:53][CH2:54][CH3:55])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].[CH:1]([P:52](=[O:59])([O:56][CH2:57][CH3:58])[O:53][CH2:54][CH3:55])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 123701-OctyneHCID 812191,3-Bis(diphenylphosphino)propaneHCID 10857821HCID 10857821, compoundHCID 21884954Dimethylphosphite

Product 2

HCID 10857821HCID 10857821, compoundHCID 54302676Diethyl oct-1-en-1-ylphosphonate

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst2×

Procedure

A mixture of 5 mmol of 1-octyne, 5 mmol of dimethylphosphite and 0.025 mmol of palladium acetate and 1,3-bis(diphenylphosphino)propane (1.5 equivalents based on the palladium acetate) was reacted at 100° C. for 6 hours in the atmosphere of nitrogen. The proton NMR analysis of the resulting reaction mixture revealed that an isomeric mixture of (a) dimethyl 1-octen-2-yl-phosphonate and (b) dimethyl 1-octen-1-yl-phosphonate was obtained with a yield of 100% and that the weight ratio of the former phosphonate (a) to the latter phosphonate (b) was 98:2.

Workup

  1. customwas reacted at 100° C. for 6 hours in the atmosphere of nitrogen
  2. customThe proton NMR analysis of the resulting reaction mixture

Sources & evidence

ORD record
ord-7984b1aba766427ebd841b43f5bc3924
Source dataset
uspto-grants-2000_08
Patent number
US06111127

Reaction notes

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