1-Propanol → HCID 10933542, compound

HRID 2371451Notes

Reaction equation

HRID 2371451 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:15](O)CC>[Ti]>[CH2:7]([O:6][P:4]([CH2:9][C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 13345Triethyl phosphonoacetate

Product 1

HCID 10933542HCID 10933542, compound

Reagents, catalysts & solvents 1

HCID 23963TitaniumCatalyst

Procedure

Titanium IV propoxide (12.1 g) was added to a stirred mixture of ethyl diethylphosphonoacetate (100.4 g) and n-propanol (610 cm3) under a nitrogen atmosphere. The mixture was stirred at the ambient temperature for a total of 18 hours, after which time analysis of the mixture showed that the reaction was complete. The volatile components were removed by distillation firstly at atmospheric pressure and then under reduced pressure on a rotary evaporator. 1.5 M aqueous hydrochloric acid (350cm3) was added to the crude product and the mixture extracted with diethyl ether. The organic layer was separated and washed with further 1.5 M aqueous hydrochloric acid solution. The aqueous phases were combined and extracted with more diethyl ether (2×100cm3). All of the organic layers were combined, washed with water and dried over anhydrous magnesium sulphate. Evaporation of the solvent under reduced pressure qave a yellow oil (85.4 g) which was used without further purification.

Workup

  1. customThe volatile components were removed by distillation firstly at atmospheric pressure
  2. customunder reduced pressure on a rotary evaporator
  3. addition1.5 M aqueous hydrochloric acid (350cm3) was added to the crude product
  4. extractionthe mixture extracted with diethyl ether
  5. customThe organic layer was separated
  6. washwashed with further 1.5 M aqueous hydrochloric acid solution
  7. extractionextracted with more diethyl ether (2×100cm3)
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customEvaporation of the solvent under reduced pressure
  11. customwas used without further purification

Sources & evidence

ORD record
ord-588baafa673146988c991c284ab219d2
Source dataset
uspto-grants-1992_03
Patent number
US05093362

Reaction notes

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