Ethanol → HCID 53961628, compound

HRID 2259456Notes

Reaction equation

HRID 2259456 reaction equation
[CH:1]([O:3][CH2:4][CH:5](O)[CH:6]=[CH2:7])=[O:2].C([C:11](CC)(CC)[C:12]([O-:15])([O-:14])[O-])C.[CH2:20](O)[CH3:21]>C(O)(=O)CC>[CH:1]([O:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:11][C:12]([O:14][CH2:20][CH3:21])=[O:15])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 10909540HCID 10909540, compoundHCID 21875354Triethylorthoaceate

Product 1

HCID 53961628HCID 53961628, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidCatalyst

Procedure

A solution of 4- formyloxy-3-hydroxy-1-butene (1.06 g, 10 mmol) and propionic acid (1 drop) in triethylorthoacetate (6 g, 40 mmol) was heated at 140° C. under conditions for distillative removal of ethanol. After 2H, the excess of ethylorthoacetate was removed by distillation in vacuo. The residue was hydrolysed with water and extracted with AcOEt. The product was purified by flash chromatography on SiO2 (eluant AcOEt: hexane, 2:8) (1 g, 60%) but distillative purification is preferred when larger quantities are involved.

Workup

  1. customAfter 2H, the excess of ethylorthoacetate was removed by distillation in vacuo
  2. extractionextracted with AcOEt
  3. distillationThe product was purified by flash chromatography on SiO2 (eluant AcOEt: hexane, 2:8) (1 g, 60%) but distillative purification

Sources & evidence

ORD record
ord-6df54fe8d79c4b9c86f08c0a7005026d
Source dataset
uspto-grants-1995_12
Patent number
US05473099

Reaction notes

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