Potassium Carbonate → 4-[(2,2-Dimethoxyethyl)sulfanyl]-3-hydroxybutan-2-one

HRID 2418016Notes

Reaction equation

HRID 2418016 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH:4]([S:9][CH2:10][CH2:11][C:12](=[O:14])[CH3:13])OC(=O)C.C([O-])([O-])=[O:18].[K+].[K+]>CO>[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][S:9][CH2:10][CH:11]([OH:18])[C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131713684HCID 131713684, compound

Product 1

HCID 204432424-[(2,2-Dimethoxyethyl)sulfanyl]-3-hydroxybutan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 200 mg. (0.8 mmol) of 2-acetoxy-3-oxobutylmercaptoacetaldehyde dimethylacetal in 2 ml. of methanol was added 110 mg. (0.8 mmol) of K2CO3. The reaction mixture was stirred 10 minutes, filtered, diluted with water and extracted with CHCl3. The CHCl3 extract was dried over Na2SO4, filtered and evaporated to 123 mg. (75%) of keto alcohol product: 1H-NMR (CDCl3) delta 2.20 (s, 3), 2.85 (m, 4), 3.32 (s, 6), 4.32 (m, 1), 4.45 (t, 1).

Workup

  1. filtrationfiltered
  2. additiondiluted with water
  3. extractionextracted with CHCl3
  4. extractionThe CHCl3 extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to 123 mg

Sources & evidence

ORD record
ord-0dde74b59a724cb4ab319a76681af98f
Source dataset
uspto-grants-1984_09
Patent number
US04471139

Reaction notes

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