Water → HCID 86747712, compound

HRID 2379533Notes

Reaction equation

HRID 2379533 reaction equation
[OH-].[Na+].[C:3]([S:6][CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])(=O)[CH3:4].[CH3:16]/[C:17](/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:18]\CCI.O>C(O)C>[CH3:18]/[C:17](/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:16]\[CH2:4][CH2:3][S:6][CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 10871691HCID 10871691, compoundHCID 12536443S-[(Diethoxyphosphoryl)methyl] ethanethioate

Product 1

HCID 86747712HCID 86747712, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Solid sodium hydroxide (0.14 g, 3.5 mmol) was added to a stirred solution of diethyl acetylthiomethylphosphonate (0.59 g, 2.5 mmol) in ethanol (10 mL). The resulting mixture was stirred at room temperature under nitrogen until all the sodium hydroxide dissolved, then added a solution of (E,E)-4,8,12-trimethyl-3,7,11-tridecatrienyl iodide (0.84 g, 2.4 mmol) in ethanol (2 mL). The resulting mixture was stirred at room temperature under nitrogen overnight. The reaction mixture was poured into cold water and extracted with ether. The ethereal extract was washed with water, dried, filtered and evaporated to give a residue, which was purified by flash chromatography on a silica gel column. Elution of the column with methylene:acetate (10:1, v:v) afforded the title compound (0.91 g, 2.26 mmol, 94%) as a colorless oil.

Workup

  1. dissolutiondissolved
  2. extractionextracted with ether
  3. extractionThe ethereal extract
  4. washwas washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue, which
  9. customwas purified by flash chromatography on a silica gel column
  10. washElution of the column with methylene:acetate (10:1, v:v)

Sources & evidence

ORD record
ord-9d1da9caa0f048a2a76ee0ea68c08e93
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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