3-(5-Fluoro-2-methylphenyl)-3-methyl-1-morpholin-4-ylbutan-1-one → 5-(5-Fluoro-2-methylphenyl)-2,5-dimethylhexan-3-one

HRID 400621Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10](N2CCOCC2)=[O:11])[CH:7]=1.[CH:21]([Li])([CH3:23])[CH3:22]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([C:8]([CH3:18])([CH3:19])[CH2:9][C:10](=[O:11])[CH:21]([CH3:23])[CH3:22])[CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-(5-fluoro-2-methylphenyl)-3-methyl-1-morpholin-4-ylbutan-1-one (200 mg, 0.716 mmol) in 2 mL of THF was treated with i-PrLi (0.7 M in pentane, 1.28 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 hour, allowed to warm to room temperature, quenched with 1 mL of methanol and 5 mL of saturated aqueous ammonium chloride solution, and extracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (100% hexanes to 25% ethyl acetate in hexanes, gradient) afforded 80.4 mg of the title product (48% yield).

Workup

temperatureto warm to room temperature
customquenched with 1 mL of methanol and 5 mL of saturated aqueous ammonium chloride solution
extractionextracted with three 50 mL portions of ethyl acetate
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-22c6f70988ff41539f6ebcad85ddfe24
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741897B2

Reaction notes

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