CID 10751188 → 1-(p-Trifluoromethylphenylsulfonyl)-2-methyl-4-acetoxy-but-2-ene

HRID 1657552Notes

Reaction equation

HRID 1657552 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[Li+].Cl[CH2:16][C:17]([CH3:24])=[CH:18][CH2:19][O:20][C:21](=[O:23])[CH3:22]>CN(C)C=O>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH2:16][C:17]([CH3:24])=[CH:18][CH2:19][O:20][C:21](=[O:23])[CH3:22])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10751188CID 10751188HCID 534009324-Chloro-3-methylbut-2-en-1-yl acetate

Product 1

HCID 543604181-(p-Trifluoromethylphenylsulfonyl)-2-methyl-4-acetoxy-but-2-ene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the sulfinic acid salt (26.0 g.) and 1-chloro-2-methyl-4-acetoxy-but-2-ene (9.75 g.) in 125 ml. of dimethylformamide was heated to 60°C. for 33/4 hours, cooled, poured into 1.21. of water and extracted with ethyl acetate. The extracts were washed with water and brine and dried. Removal of the solvent afforded 18.72 g. of the desired product. Chromatography of a 3.5 g. portion on silica gel gave 3.25 g. of the 1-(p-trifluoromethylphenylsulfonyl)-2-methyl-4-acetoxy-but-2-ene as a colorless oil. Anal. calcd. for C14H15F3O4S: C 50.00, H 4.50, S 9.53; found C 49.77, H 4.68, S 9.71%.

Workup

  1. temperaturecooled
  2. additionpoured into 1.21
  3. extractionof water and extracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. customdried
  6. customRemoval of the solvent
  7. customafforded 18.72 g

Sources & evidence

ORD record
ord-aac94c316456443784805d6c624ad46b
Source dataset
uspto-grants-1976_06
Patent number
US03960967

Reaction notes

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