Triethylamine → HCID 53995472, compound

HRID 1702001Notes

Reaction equation

HRID 1702001 reaction equation
Br[CH:2]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].C(N(CC)CC)C>CC(C)=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:3]([S:4]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5])=[CH:2][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13048613HCID 13048613, compound

Product 1

HCID 53995472HCID 53995472, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 9.6 g of 2-bromo-1-(2,4-dichlorophenyl)-4,4-dimethyl-1-phenylsulfonylpentan-3-one and 2.23 g of triethylamine in 100 ml of acetone was refluxed for 3 hours. The mixture was poured into ice water and extracted with 150 ml of ethyl acetate. The organic layer was washed twice with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of n-hexane (20 parts) and acetone (1 part) to give 4.8 g of 1-(2,4-dichlorophenyl)-4,4-dimethyl-1-phenylsulfonyl-1-penten-3-one. nD25 1.5723

Workup

  1. extractionextracted with 150 ml of ethyl acetate
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additiona mixture of n-hexane (20 parts) and acetone (1 part)

Sources & evidence

ORD record
ord-9de6e6f18bdd455687d55981acb2f0aa
Source dataset
uspto-grants-1983_04
Patent number
US04379921

Reaction notes

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