Potassium Carbonate → HCID 14743494, compound

HRID 1073894Notes

Reaction equation

HRID 1073894 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[C:13]([CH3:17])([C:15]#[CH:16])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][C:13]([CH3:17])([O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)[C:15]#[CH:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 706791-Butyne, 3-chloro-3-methyl-2×

Product 1

HCID 14743494HCID 14743494, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.62 g of 4-(trifluoromethyl)phenol, 1.53 g of 2-chloro-2-methyl-3-butyne and 10 g of potassium carbonate were heated at reflux in 50 ml of acetone. After 18, 42 and 66 hours further batches of 1.53 g of 2-chloro-2-methyl-3-butyne were added. 72 hours after the final addition the mixture was allowed to cool to room temperature and was partitioned between diethyl ether and water. The organic phase was washed with aqueous sodium hydroxide solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 5% (v/v) ethyl acetate/petroleum ether for the elution. 1.8 g of 4-(1,1-dimethyl-2-propynyloxy)trifluoromethylbenzene were obtained as a yellow oil.

Workup

  1. addition72 hours after the final addition the mixture
  2. customwas partitioned between diethyl ether and water
  3. washThe organic phase was washed with aqueous sodium hydroxide solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using 5% (v/v) ethyl acetate/petroleum ether for the elution

Sources & evidence

ORD record
ord-40450f66d34345d4b37c43a4ff33b86d
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

Loading…