Hydrochloric Acid → HCID 60108854, compound

HRID 1246835Notes

Reaction equation

HRID 1246835 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[C:20]([F:23])([F:22])[F:21])([CH3:3])[CH3:2].[H-].[Na+].[C:26](=O)([O:30]CC)[O:27][CH2:28][CH3:29].Cl>C1COCC1>[CH2:28]([O:27][C:26](=[O:30])[CH2:18][C:17]([C:14]1[CH:15]=[CH:16][C:11]([S:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:1]([CH3:3])[CH3:2])=[C:12]([C:20]([F:23])([F:21])[F:22])[CH:13]=1)=[O:19])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 21906747HCID 21906747, compound

Product 1

HCID 60108854HCID 60108854, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Then, 3-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3-oxo-propionic acid ethyl ester 45 was prepared as follows. To a solution of compound 44 (11.5 g, 34.0 mmol) in THF (150 mL) was added 60% sodium hydride in mineral oil (1.84 g, 40.8 mmol). The mixture was stirred at room temperature for 10 minutes. Diethyl carbonate (46.5 mL, 340 mmol) was added and the mixture was heated under reflux for 2 hours. 10% HCl aq. (100 mL) was added and the solution was extracted with ethyl acetate (200 mL). The organic layer was separated, washed with brine (5×250 mL), dried over MgSO4 and filtered. The filtrate was concentrated on a rotor-vapor to give a brown oil 45 (10.6 g, 76%); MS (DCI) m/z 411 (M+H)+; 428 (M+NH4)+.

Workup

  1. customThen, 3-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-3-oxo-propionic acid ethyl ester 45 was prepared
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionthe solution was extracted with ethyl acetate (200 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (5×250 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated on a rotor-vapor

Sources & evidence

ORD record
ord-ee304f1b15c34e04b1ce2ed2f14329c7
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Reaction notes

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