Hydrochloric Acid → HCID 11049452, compound

HRID 1826081Notes

Reaction equation

HRID 1826081 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH2:8][C:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([CH2:26][CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])=[O:7])[CH3:4].[F:28][C:29]([F:39])([F:38])[C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Br)=[CH:32][CH:31]=1.Cl>O1CCCC1>[CH2:3]([O:5][C:6]([CH:8]([CH2:34][C:33]1[CH:32]=[CH:31][C:30]([C:29]([F:28])([F:38])[F:39])=[CH:37][CH:36]=1)[C:9]([C:11]1[CH:12]=[C:13]([CH2:19][CH:20]([CH2:26][CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])=[O:10])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 11727819HCID 11727819, compound

Product 1

HCID 11049452HCID 11049452, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere, stirring and cooling with ice, sodium hydride (60% oil dispersion, 296 mg, 7.40 mmol) was added little by little to a solution of ethyl 3-[3-(2-ethoxycarbonylacetyl)-4-methoxyphenyl]-2-ethylpropanoate (2.59 g, 7.39 mmol) in anhydrous tetrahydrofuran (30 mL), and then the mixture was stirred for 20 minutes under cooling with ice and for 30 minutes at room temperature. Following this, a solution of 4-(trifluoromethyl)benzylbromide (1.77 g, 7.40 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise. After completion of the dropwise addition, the mixture was refluxed for 6 hours. After cooling, a mixture of 1 mol/L hydrochloric acid (15 mL) with ice water (100 mL) was added thereto, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=8:1 v/v) to afford 3.70 g (98%) of the title compound as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. additionwas added dropwise
  3. additionAfter completion of the dropwise addition
  4. temperaturethe mixture was refluxed for 6 hours
  5. temperatureAfter cooling
  6. additionwas added
  7. extractionwhich was extracted with ethyl acetate
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=8:1 v/v)

Sources & evidence

ORD record
ord-64ef77ce43004f3c8887bd52f5e8b44e
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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