Methyl iodide → HCID 90111330, compound

HRID 1500235Notes

Reaction equation

HRID 1500235 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[CH3:9][CH:10]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].CI>C1COCC1>[CH3:9][C:10]([CH3:2])([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 90111382Benzenepropanoic acid, α-methyl-4-(trifluoromethyl)-, ethyl ester

Product 1

HCID 90111330HCID 90111330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LDA (2.9 mL of 2 M) in THF (30 mL) at −78° C. add ethyl 2-methyl-3-[4-(trifluoromethyl)phenyl]propanoate (1 g, 3.85 mmol). Stir for 10 min, then add methyl iodide (1.48 g, 10.4 mmol) and stir for an additional 15 min Quench the reaction with 10 mL of 1 N HCl and allow to warm to ambient temperature. Extract with EtOAc (50 mL). Wash extract with brine, dry over sodium sulfate, filter, and concentrate. Purify the residue by flash chromatography (5% EtOAc in petroleum ether) to give the title compound (475 mg).

Workup

  1. customQuench
  2. customthe reaction with 10 mL of 1 N HCl
  3. extractionExtract with EtOAc (50 mL)
  4. washWash
  5. extractionextract with brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the residue by flash chromatography (5% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-67a575b6188c4509a90c2d0e5b1497b0
Source dataset
uspto-grants-2015_12
Patent number
US09206139B2

Reaction notes

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