Dimethyl Sulfoxide → HCID 14536797, compound

HRID 703148Notes

Reaction equation

HRID 703148 reaction equation
CS(C)=O.[H-].[Na+].[SH:7][CH2:8][CH2:9][OH:10].Br[CH2:12][CH2:13][C:14]([CH3:22])([CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>O>[OH:10][CH2:9][CH2:8][S:7][CH2:12][CH2:13][C:14]([CH3:21])([CH3:22])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 14536796HCID 14536796, compound

Product 1

HCID 14536797HCID 14536797, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 ml. dimethyl sulphoxide and 42.2 mmol sodium hydride is maintained at 80° C. for 45 minutes. It is then cooled to ambient temperature, 3.3 g. (42,2 mmol) 2-mercaptoethanol and then 10.0 g. (42,2 mmol) ethyl 5-bromo-3,3-dimethylpentanoate are added thereto and the reaction mixture is stirred for 3 hours at ambient temperature. It is then poured into water and extracted with diethyl ether. The ethereal phase is dried with anhydrous sodium sulphate and then evaporated. After chromatography of the residue on silica gel with a mixture of equal parts by volume of diethyl ether and cyclohexane, there are obtained 6.8 g. (70% of theory) of the desired product in the form of a colourless oil.

Workup

  1. additionA mixture of 50 ml
  2. extractionextracted with diethyl ether
  3. dry with materialThe ethereal phase is dried with anhydrous sodium sulphate
  4. customevaporated
  5. additionAfter chromatography of the residue on silica gel with a mixture of equal parts by volume of diethyl ether and cyclohexane, there
  6. customare obtained 6.8 g

Sources & evidence

ORD record
ord-f6d0adb96cfa4247bb225f68d26ad3c0
Source dataset
uspto-grants-1991_01
Patent number
US04981873

Reaction notes

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