반응 #935591

반응 방정식

butyl lithium

o-chloroanisole

ethyl iodide

butyl lithium

2,2,6,6-tetramethylpiperidine

N-methylcaprolactam

→

3-ethylhexahydro-3-(3 -methoxyphenyl)-1-methyl-2H-azepin-2-one

용매

tetrahydrofuran

hexane

THF

hexane

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 15 minutes
2. 2
   workup.STIRRINGthe mixture stirred for 1.5 hours
3. 3
   workup.WAITAfter one hour
4. 4
   기타the reaction was quenched with water (100 ml)
5. 5
   기타the solvents removed under reduced pressure
6. 6
   기타The residue was partitioned between 2 N HCl (200 ml) and toluene (250 ml)
7. 7
   세척The organic layer was washed with brine
8. 8
   기타dried
9. 9
   기타the solvents removed under reduced pressure

실험 절차

a solution of butyl lithium (0.05 mole) in hexane (31.25 ml) was treated with 2,2,6,6-tetramethylpiperidine (8.5 ml), followed by dry tetrahydrofuran ("THF"; 100 ml) under an inert atmosphere at 0° C. The mixture was treated with a solution of N-methylcaprolactam (6.25 ml, 50 mM) in THF (20 ml) and stirred for 30 minutes. A solution of butyl lithium (0.05 mole) in hexane (31.25 ml), was added and the mixture stirred for 15 minutes. A solution of o-chloroanisole (6.2 ml) in THF (20 ml) was added slowly, the mixture stirred for 1.5 hours and treated with ethyl iodide (5.15 ml). After one hour, the reaction was quenched with water (100 ml) and the solvents removed under reduced pressure. The residue was partitioned between 2 N HCl (200 ml) and toluene (250 ml). The organic layer was washed with brine, dried and the solvents removed under reduced pressure, to give 3-ethylhexahydro-3-(3 -methoxyphenyl)-1-methyl-2H-azepin-2-one (5.5 g) b.p. 140°/0.1 mm. Recrystallisation from diisopropyl ether gave pure title compound (5.0 g) m.p. 68°-69° C., identical with authentic material.

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