Acetyl chloride → HCID 14348020, compound

HRID 1493516Notes

Reaction equation

HRID 1493516 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-3b01d2e3eb3d46b9b16177eb490b6842
Source dataset
uspto-grants-1991_06
Patent number
US05021579

Reaction notes

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