Methanethiol → Ethyl 2-ethylthiomethyl-4-methylpentanoate

HRID 374700Notes

Reaction equation

HRID 374700 reaction equation
[CH2:1]([C:5](=[CH2:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:2]([CH3:4])[CH3:3].C[C:13]([CH3:16])([O-])C.[K+].C[SH:19]>C(OCC)(=O)C>[CH2:13]([S:19][CH2:11][CH:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:16]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 10909818Ethyl 4-methyl-2-methylenepentanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22418875Ethyl 2-ethylthiomethyl-4-methylpentanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

650 mg of ethyl 2-isobutyl-2-propenoate was dissolved in 3 ml of methylmercaptan, and 50 mg of potassium tert-butoxide was added thereto. The mixture was stirred at room temperature for two hours. The reaction solution was diluted with 60 ml of ethyl acetate, washed with water and then with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 660 mg of ethyl 2-ethylthiomethyl-4-methylpentanoate as colorless oily substance.

Workup

  1. washwashed with water
  2. dry with materialwith a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0611cdcfcdfa4a28afd654b3317d8f93
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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