Diethyl Ether → HCID 21423425, compound

HRID 259201Notes

Reaction equation

HRID 259201 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5][O:6][CH2:7][CH2:8][CH3:9])=[O:4].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C>C(Cl)(Cl)Cl>[Cl-:1].[O:4]=[C:3]([CH2:5][O:6][CH2:7][CH2:8][CH3:9])[CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 21423413HCID 21423413, compound

Product 1

HCID 21423425HCID 21423425, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-chloro-3-propoxyacetone (8.5 g.) and triphenylphosphine (15.6 g.) in chloroform (20 ml.) was saturated with nitrogen and heated at reflux under nitrogen overnight. An excess of dry diethyl ether was added, and then the solvents were decanted from the gum that separated. The remaining solvent was removed in vacuo to give crude 2-oxo-3-propoxypropyltriphenylphosphonium chloride (14.9 g.). This was stirred vigorously with a solution of sodium carbonate (14.6 g.) in water (146 ml.) for 24 hours. The solution was extracted with diethyl ether and the ethereal extracts dried over sodium sulphate. The solvent was removed by evaporation, and the residue was triturated with petroleum to give propoxyacetylmethylenetriphenylphosphorane (6.3 g.), a sticky solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen overnight
  3. customthe solvents were decanted from the gum
  4. customthat separated
  5. customThe remaining solvent was removed in vacuo

Sources & evidence

ORD record
ord-8ee2b51beeee460e92995f6e01c74bc5
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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