Acetyl chloride → HCID 14348020, compound

HRID 414032Notes

Reaction equation

HRID 414032 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][CH:12]2[CH2:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>O1CCCC1>[C:29]([O:18][C:16]1[CH2:17][CH:12]([CH2:11][CH2:10][S:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:1])[F:21])=[CH:8][CH:7]=2)[CH2:13][C:14](=[O:19])[CH:15]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14517858HCID 14517858, compound

Product 1

HCID 14348020HCID 14348020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.32 Grams of 5-[2-(4-trifluoromethylphenylthio)ethyl]cyclohexane-1,3-dione was dissolved in 50 ml of tetrahydrofuran, and 2.12 g of triethylamine was added. Thereafter, 1.73 g of acetyl chloride was added dropwise with thorough stirring under ice-cooling. After continuing stirring for further 2 hours at room temperature, the precipitated solid was filtered off. The solvent was removed from the filtrate, and the residue was dissolved in ether. The ether layer was successively washed with dilute hydrochloric acid, aqueous sodium hydrogencarbonate and water and dried over anhydrous magnesium sulfate. Ether was removed to obtain 7.13 g of 1-acetoxy-5-[2-(4-trifluoromethylphenylthio)ethyl]-1-cyclohexene-3-one.

Workup

  1. temperaturecooling
  2. stirringAfter continuing stirring for further 2 hours at room temperature
  3. filtrationthe precipitated solid was filtered off
  4. customThe solvent was removed from the filtrate
  5. dissolutionthe residue was dissolved in ether
  6. washThe ether layer was successively washed with dilute hydrochloric acid, aqueous sodium hydrogencarbonate and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customEther was removed

Sources & evidence

ORD record
ord-220d77b27c964157a1e478bfc5365cff
Source dataset
uspto-grants-1988_12
Patent number
US04789396

Reaction notes

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