Sodium Bicarbonate → Tert-butyl 5,5,5-trifluoro-3-methyl-2-(4-methylphenyl)pentanoate

HRID 877201Notes

Reaction equation

HRID 877201 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][CH:4]([CH3:16])[CH:5]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7].ClC(Cl)(Cl)C(=N)O[C:23]([CH3:26])([CH3:25])[CH3:24].C1CCCCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]([F:17])([F:18])[CH2:3][CH:4]([CH3:16])[CH:5]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)[C:6]([O:8][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:7]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 21867204Cyclohexane ethylacetateHCID 581363615,5,5-Trifluoro-3-methyl-2-(4-methylphenyl)pentanoic acid

Product 1

HCID 58136758Tert-butyl 5,5,5-trifluoro-3-methyl-2-(4-methylphenyl)pentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under argon, 3.79 g (14.5 mmol) of 5,5,5-trifluoro-3-methyl-2-(4-methylphenyl)pentanoic acid were dissolved in 60 ml of THF at room temperature, and 27 μl (0.22 mmol) of a 1 M boron trifluoride/diethyl ether complex solution were added. 3.828 g (17.48 mmol) of tert-butyl 2,2,2-trichloroethanimidoate were then metered in a little at a time, and the mixture was stirred at room temperature overnight. After the reaction had gone to completion (monitored by TLC; mobile phase cyclohexane/ethyl acetate 2:1), 2 g of solid sodium bicarbonate were added with vigorous stirring of the reaction solution. The reaction mixture was then filtered, and the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 5:1). This gave 3.25 g (10.27 mmol, 71% of theory) of the title compound as a colorless oil.

Workup

  1. addition27 μl (0.22 mmol) of a 1 M boron trifluoride/diethyl ether complex solution were added
  2. additionwere added
  3. stirringwith vigorous stirring of the reaction solution
  4. filtrationThe reaction mixture was then filtered
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-d1049ab1adc742e8909c5243d6d1fc3f
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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