Ammonium Chloride → HCID 14001754, compound
Reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)(=O)=O.[CH2:17]([Mg]Br)[CH:18]([CH3:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.CN1CCCC1=O.C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.C/C(/[O-])=C\C(C)=O.[Fe+3]>[CH2:17]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)[CH:18]([CH3:20])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of the compound (2 g) prepared in Example 32 in tetrahydrofuran (35 mL), 1-methyl-2-pyrrolidone (5.2 mL), tris(2,4-pentanedionato)iron(III) (413.5 mg), and isobutyl magnesium bromide (2M diethyl ether solution, 4.68 mL) were added thereto, followed by stirring at room temperature for 4 hours. The reaction mixture was added with a saturated aqueous ammonium chloride solution and the mixture was extracted with t-butyl methyl ether. The organic layer was successively washed with a saturated aqueous ammonium chloride solution, water, and brine, dried and concentrated. Thus, the obtained residue was purified by silica gel column chromatography (hexane:tetrahydrofuran=50:1 to 20:1) to thereby give the title compound (922.5 mg) having the following physical properties.
Workup
- extractionthe mixture was extracted with t-butyl methyl ether
- washThe organic layer was successively washed with a saturated aqueous ammonium chloride solution, water, and brine
- customdried
- concentrationconcentrated
- customThus, the obtained residue was purified by silica gel column chromatography (hexane:tetrahydrofuran=50:1 to 20:1)
Sources & evidence
- ORD record
- ord-5a3c78d7cbe04c37844b3b2c00793a90
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653305B2
Reaction notes
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