Potassium Carbonate → (2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

HRID 252156Notes

Reaction equation

HRID 252156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][S:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 849893-Methoxybenzenethiol

Product 1

HCID 13642516(2,2-Diethoxyethyl)(3-methoxyphenyl)sulfaneYield 102.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Methoxythiophenol (10.00 g, 71.33 mmol), bromoacetaldehyde diethyl acetal (11.47 mL, 76.24 mmol), potassium carbonate (10.35 g, 74.89 mmol) and acetone (100 mL) were stirred at ambient temperature under nitrogen for 3 h. The white suspension was filtered, washed with acetone (2×25 mL) and the combined filtrate and washings concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed with 0.5N NaOH (aq.) (2×15 mL), water 15 mL) and brine (15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo and then further dried at 130° C. under high vacuum to give the title compound (18.74 g, quantitative).

Workup

  1. filtrationThe white suspension was filtered
  2. washwashed with acetone (2×25 mL)
  3. concentrationthe combined filtrate and washings concentrated to dryness in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  5. washwashed with 0.5N NaOH (aq.) (2×15 mL), water 15 mL) and brine (15 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customfurther dried at 130° C. under high vacuum

Sources & evidence

ORD record
ord-df044493699e4870889ddbeb63aaea1f
Source dataset
uspto-grants-2011_01
Patent number
US07868017B2

Reaction notes

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