Methyl morpholine oxide → [4-(4-Chlorophenoxy)-2-propylphenyl][4-chloro-2-fluoro-5-methoxyphenyl]methanone
Reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[CH:14][C:13]=2[CH2:26][CH2:27][CH3:28])[OH:11])=[C:4]([F:29])[C:3]=1[Si](C)(C)C.C[N+]1([O-])CCOCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C(OCC)C.C1COCC1.C(OCC)(=O)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:10]([C:5]3[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[CH:3][C:4]=3[F:29])=[O:11])=[C:13]([CH2:26][CH2:27][CH3:28])[CH:14]=2)=[CH:24][CH:23]=1Participants
9
Reactant 3
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 25 °C
Procedure
A mixture of the product from Step 2 (1.9 g, 3.7 mmol), N-methylmorpholine-N-oxide (0.70 g, 6.0 mmol), tetrapropylammonium perruthenate (70 mg, 0.2 mmol) and 4 Å molecular sieves (2.0 g) in dichloromethane (20 mL) was stirred at 25° C. for 1 h. The reaction mixture was diluted with diethyl ether (60 mL) and filtered through a short path of silica gel. Removal of the solvent gave the crude product. The crude product was dissolved in THF (20 mL) and treated with tetrabutylammonium fluoride (1M in THF, 5.6 mL, 5.6 mmol) for 10 min. The reaction mixture was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified by chromatography on silica gel to give the title product.
Workup
- filtrationfiltered through a short path of silica gel
- customRemoval of the solvent
- customgave the crude product
- washwashed with brine
- customdried
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel
Sources & evidence
- ORD record
- ord-b99a6ec23c2e45b0893015d613d683f8
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834036B2
Reaction notes
Loading…