Isopropyl iodide → 2-(3,5-Bis-trifluoromethyl-phenyl)-3-methyl-butyric Acid Methyl Ester

HRID 478677Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13](=[O:29])[CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1.[CH:30](I)([CH3:32])[CH3:31]>C1COCC1>[CH3:11][O:12][C:13](=[O:29])[CH:14]([C:15]1[CH:16]=[C:17]([C:25]([F:28])([F:26])[F:27])[CH:18]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:20]=1)[CH:30]([CH3:32])[CH3:31]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium bis(trimethylsilyl) amide (1.0M in THF—177 μL) was added drop-wise to a solution of (3,5-bis-trifluoromethyl-phenyl)-acetic acid methyl ester (389 mg) in dry THF (2 mL) at 0° C., under nitrogen atmosphere. After ten minutes, isopropyl iodide (143 μL) was added and the reaction mixture was stirred at 0° C. for 30 min. Further isopropyl iodide (143 μL) was added and the solution stirred at r.t. for 1 hour. The reaction was quenched with a 2N hydrochloric acid solution (2 mL) and the product was extracted with Et2O (2×). The combined organic extracts were dried and concentrated in vacuo to a residue which was purified by flash chromatography (CH/AcOEt 95:5) to give the title compound (184 mg) as a colourless oil.

Workup

waitAfter ten minutes
stirringthe solution stirred at r.t. for 1 hour
customThe reaction was quenched with a 2N hydrochloric acid solution (2 mL)
extractionthe product was extracted with Et2O (2×)
customThe combined organic extracts were dried
concentrationconcentrated in vacuo to a residue which
customwas purified by flash chromatography (CH/AcOEt 95:5)

Sources & evidence

ORD record: ord-be6c99b2b16b4f939114963e9941791e
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642240B2

Reaction notes

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