Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:7][CH2:6]1)=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH3:1][O:2][C:3]([CH:5]1[CH2:6][CH2:7][CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[CH2:9][CH2:10]1)=[O:4]Participants
4
Procedure
In an 18 mL vial with stir bar and 4-(2-fluorobenzoyl)cyclohexanecarboxylic acid methyl ester (333 mg; 1.2 mmol), trifluoroacetic acid (4 mL) was chilled to 0° C. and triethylsilane (700 mg; 6.0 mmol) was added over 1 minute. Mixture was allowed to warm to room temperature. After 48 hours, mixture was concentrated in vacuo and reduced by half volume. Mixture was poured into cold KOH solution and pH adjust further to pH 6. Aqueous mixture was extracted 3×5 mL ethyl acetate. Combined ethyl acetate was washed with brine and dried over MgSO4. Crude oil was purified via (20:1) flash chromatography 0-10% ethyl acetate in hexanes to give 250 mg of title compound. (83% yield).
Workup
- concentrationmixture was concentrated in vacuo
- additionMixture was poured into cold KOH solution
- extractionAqueous mixture was extracted 3×5 mL ethyl acetate
- washCombined ethyl acetate was washed with brine
- dry with materialdried over MgSO4
- customCrude oil was purified via (20:1) flash chromatography 0-10% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-eb8677f7660f4a8b9165adf123a9adfd
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985755B2
Linked notes
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