Potassium Carbonate → HCID 18689869, compound

HRID 1456963Notes

Reaction equation

HRID 1456963 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16]>CC(C)=O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][S:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162573-ChlorothiophenolHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 18689869HCID 18689869, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirring mixture of 20.0 gm (0.138 mol) 3-chlorothiophenol and 21.0 gm (0.15 mol) potassium carbonate in 220 mL acetone were added dropwise 1.1 equivalents of bromoacetaldehyde diethyl acetal. After stirring for 17 hours at ambient temperature, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The resulting residue was partitioned between diethyl ether and water. The organic phase was separated, washed with saturated sodium chloride, dried over sodium sulfate and concentrated under reduced pressure to give 35.1 gm (97%) of the desired. compound as a rust colored oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe resulting residue was partitioned between diethyl ether and water
  4. customThe organic phase was separated
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give 35.1 gm (97%) of the

Sources & evidence

ORD record
ord-fbe6e5c162ae401c88f038e92364f9e7
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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