25383-05-5 → HCID 12985179, compound

HRID 1706171Notes

Reaction equation

HRID 1706171 reaction equation
[CH:1](/[P:4](=[O:15])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:2]/[CH3:3].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH:1](/[P:4](=[O:15])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:2]\[CH3:3]

Participants

4

Reactant 2

HCID 987801225383-05-5HCID 23665647Potassium tert-butoxide

Product 1

HCID 12985179HCID 12985179, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(1)-1 Di-tert.-butyl cis-1-propenylphosphonate (15.0 g.) was added to a solution of potassium tert.-butoxide in tert.-butyl alcohol (K: 250 mg., tert.-C4H9OH: 150 ml.) and then the mixture was stirred for 6 hours at 55°-60° C. The resultant mixture was concentrated under reduced pressure and the residue was shaken with a mixture of ethyl acetate (400 ml.) and ice-water (100 ml.). The ethyl acetate layer was separated, washed with water (50 ml.), dried over magnesium sulfate and evaporated to dryness under reduced pressure to give oily residue (13.34 g.), which was distilled under reduced pressure to give oily di-tert.-butyl trans-1-propenylphosphonate (12 g.), b.p. 78°-80° C./2 mmHg.

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. stirringthe residue was shaken with a mixture of ethyl acetate (400 ml.) and ice-water (100 ml.)
  3. customThe ethyl acetate layer was separated
  4. washwashed with water (50 ml.)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto give oily residue (13.34 g.), which
  8. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-213d5f0a78af4b639c204506b9cc4302
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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