Ethanethiol → Ethyl phytyl thioether

HRID 2254656Notes

Reaction equation

HRID 2254656 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].[CH2:6](Cl)/[CH:7]=[C:8](/[CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH3:19])[CH3:14])\[CH3:9]>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([S:5][CH2:3][CH3:4])/[CH:7]=[C:8](/[CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][C@@H:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH3:19])[CH3:14])\[CH3:9]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 11130851Phytyl chloride

Product 1

HCID 131718073Ethyl phytyl thioetherYield 92.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.84 g of sodium hydride was added to a solution of 2.40 g of ethylmercaptan dissolved in 30 ml of N,N-dimethylformamide. Thereinto was dropped 10.00 g of phytyl chloride at 40° C. The resulting mixture was stirred at the same temperature for 3 hours. After the completion of the reaction, the resulting mixture was concentrated under reduced pressure. The residue obtained was dissolved in 30 ml of ethyl acetate. The resulting solution was washed with 1N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: n-hexane:ethyl acetate=9:1) to obtain 10.00 g (yield: 92%) of oily ethyl phytyl thioether.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. customThe residue obtained
  4. washThe resulting solution was washed with 1N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue obtained
  8. customwas purified by a column chromatography (eluant: n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f13fab5a0bc047c681b65a8edbb4cd91
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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