Methanethiol → Ethyl 2-ethylthiomethyl-4-methylpentanoate

HRID 893137Notes

Reaction equation

HRID 893137 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-354216cfd205480e8ee97a22d9cfb8a3
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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