Water → S-2-hydroxy-2-methylpropyl ethanethioate

HRID 536762Notes

Reaction equation

HRID 536762 reaction equation
Cl[CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[C:7](=[S:10])([O-:9])[CH3:8].[K+].O>CN(C=O)C.[Br-].[Na+]>[C:7](=[O:9])([S:10][CH2:2][C:3]([OH:5])([CH3:6])[CH3:4])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 684091-Chloro-2-methylpropan-2-olHCID 23670855Potassium ethanethioate

Product 1

HCID 86639997S-2-hydroxy-2-methylpropyl ethanethioateYield 113.2%

Reagents, catalysts & solvents 2

HCID 253881Sodium BromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-chloro-2-methylpropan-2-ol (2.2 g, 20.26 mmol) and potassium ethanethioate (6.94 g, 60.8 mmol) in DMF (20 mL) was added 100 mg of sodium bromide and the resulting mixture was heated at 50° C. for 18 hours. The mixture was then poured into water and extracted with EtOAc. The acetate layer was washed with water, brine, dried with MgSO4 and concentrated under reduced pressure to provide 3.4 g of the title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe acetate layer was washed with water, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac46324ed30b40c9b8e3c859a54808c1
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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