Water → Ethyl [(2,2-diethoxyethyl)sulfanyl]acetate

HRID 1061663Notes

Reaction equation

HRID 1061663 reaction equation
[O-]CC.[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16]Br)[CH3:13].O>C(O)C>[CH2:12]([O:14][CH:15]([O:18][CH2:19][CH3:20])[CH2:16][S:7][CH2:6][C:5]([O:9][CH2:10][CH3:11])=[O:8])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 12185Ethyl ThioglycolateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2723922Sodium ethoxide

Product 1

HCID 22284188Ethyl [(2,2-diethoxyethyl)sulfanyl]acetateYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (2.83 g) is added to a solution of ethyl thioglycolate (5.00 g) and bromoacetaldehyde diethylacetal (8.20 g) in ethanol (150 ml), and the mixture is refluxed for three hours. The reaction mixture is allowed to stand at room temperature, water is added to the mixture, and the whole is extracted with diethyl ether. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (5.75 g).

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. customto stand at room temperature
  3. extractionthe whole is extracted with diethyl ether
  4. washThe extract is washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-98ee6c5626aa435387c98c317bbb2e7e
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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