Ethyl Acetate → HCID 15289909, compound

HRID 1975692Notes

Reaction equation

HRID 1975692 reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[CH:20](Br)[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23].C(OCC)(=O)C>C(Cl)Cl>[Cl:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[CH:20]([N:7]1[CH2:8][CH2:9][C:10]2[S:2][CH:3]=[CH:4][C:5]=2[CH2:6]1)[C:21](=[O:26])[C:22]([F:24])([F:25])[F:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chlorideHCID 152899323-Bromo-3-(2-chlorophenyl)-1,1,1-trifluoro-2-propanone

Product 1

HCID 15289909HCID 15289909, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10 ml of methylene chloride were added to 0.39 g (2.6 mmole) of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride and 0.28 g (2.6 mmole) of sodium carbonate, and then a solution of 0.67 g (2.2 mmole) of 2-chloro-α-trifluoroacetylbenzyl bromide in 10 ml of methylene chloride was slowly added to the resulting mixture, whilst stirring at room temperature. The mixture was then stirred at room temperature for 3 hours. At the end of this time, 200 ml of ethyl acetate were added to the reaction mixture, and the organic layer was separated, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was subjected to silica gel column chromatography, using a 100:4 by volume mixture of toluene and ethyl acetate as the eluent, to give 0.31 g of the title compound as a colorless oil.

Workup

  1. stirringThe mixture was then stirred at room temperature for 3 hours
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. additionby volume mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3b1533ff312b4269ac1c6b8b428b51de
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

Loading…