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

HRID 1632595Notes

Reaction equation

HRID 1632595 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-462aacf1c3114eb381564d0afeaec30a
Source dataset
uspto-grants-1984_10
Patent number
US04476312

Reaction notes

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