Dichloromethane → HCID 58288163, compound

HRID 1476130Notes

Reaction equation

HRID 1476130 reaction equation
[F:1][C:2]([F:20])([F:19])[C@H:3]([CH3:18])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].COCCOC.[Cl:27][C:28]([Cl:33])(Cl)[C:29](Cl)=[O:30].ClCCl>C(OCC)C.[Cu].[Zn]>[Cl:27][C:28]1([Cl:33])[C:29](=[O:30])[CH2:17][CH:16]1[C:13]1[CH:12]=[CH:11][C:10]([CH:4]([C@@H:3]([CH3:18])[C:2]([F:1])([F:19])[F:20])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6420Trichloroacetyl chlorideHCID 80711,2-DimethoxyethaneHCID 58288259HCID 58288259, compound

Product 1

HCID 58288163HCID 58288163, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent

Procedure

3.83 g (13.38 mmol) of ethyl (3R)-4,4,4-trifluoro-3-methyl-2-(4-vinylphenyl)butanoate were dissolved in 50 ml of diethyl ether, and 2.67 g (20.74 mmol) of zinc-copper couple and 6.5 ml of 1,2-dimethoxyethane were added in succession. 4 ml (36.1 mmol) of trichloroacetyl chloride were then slowly added dropwise to the suspension obtained. The reaction solution was then heated under reflux and stirred overnight. After addition of dichloromethane, the reaction mixture was washed successively with water and saturated sodium chloride solution. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product obtained was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gave 4.57 g (86% of theory) of the title compound in the form of a yellowish oil which was used without further characterization in subsequent reactions.

Workup

  1. customobtained
  2. temperatureThe reaction solution was then heated
  3. temperatureunder reflux
  4. washthe reaction mixture was washed successively with water and saturated sodium chloride solution
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b9cc09132bd4bd4bb8712a279744292
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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