Methanethiol → Ethyl 2-ethylthiomethyl-4-methylpentanoate

HRID 1720666Notes

Reaction equation

HRID 1720666 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-b260e60e8d42432c9ae1c67fa8bcd51f
Source dataset
uspto-grants-1996_04
Patent number
US05506356

Reaction notes

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