Toluene → HCID 66765168, compound
Reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:11]=[C:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[O:14][C:15]([F:18])([F:17])[F:16])[C:7](OC)=[O:8])[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[C:12]([CH:19]3[CH2:21][CH2:20]3)[C:13]=2[O:14][C:15]([F:17])([F:18])[F:16])[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Methyl 3,5-dicyclopropyl-4-(trifluoromethoxy)benzoate (259 mg, 0.863 mmol) was dissolved in DCM (8.6 mL) and the mixture was cooled to 0° C. DIBAL in toluene (1.73 mL, 1.73 mmol) was added and the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was quenched with the addition of 3N HCl and water. The mixture was stirred vigorously for 30 minutes and extracted with DCM. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (0-30% EtOAc/hexanes) to yield the title compound as a clear oil (190 mg).
Workup
- temperatureto warm to room temperature
- customThe reaction mixture was quenched with the addition of 3N HCl and water
- stirringThe mixture was stirred vigorously for 30 minutes
- extractionextracted with DCM
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (0-30% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-88b86bf79aa641d89be6afeb24424d9f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742110B2
Reaction notes
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