반응 #516248

반응 방정식

2-chloroanisole

1-Trimethylsilanyl-azepan-2-one

1-trimethylsilanyl-azepan-2-one

n-BuLi

hexane

n-BuLi

hexane

2,2,6,6-tetramethyl piperidine

→

title compound

3-(3-methoxy-phenyl)-azepan-2-one

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGAfter stirring for 30 min under Ar
3. 3
   기타the reaction was quenched with H2O
4. 4
   workup.STIRRINGstirred for 30 min
5. 5
   농축concentrated in vacuo
6. 6
   workup.ADDITIONdiluted with EtOAc
7. 7
   세척washed with 5N HCl (100 mL) and brine
8. 8
   건조The organic layer was dried (MgSO4)
9. 9
   농축concentrated
10. 10
    기타purified

실험 절차

To 1.6 M n-BuLi in hexane (31.3 mL, 50 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (8.43 mL, 50 mmol) in anhydrous THF (100 mL) over 5 min. 1-Trimethylsilanyl-azepan-2-one (as described in Step F above) (9.26 g, 50 mmol) in anhydrous THF (20 mL) was added. After stirring the reaction mixture for 10 min a further portion of 1.6M n-BuLi in hexane (31.3 mL, 50 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (6.34 mL, 50 mmol) was added. After stirring for 30 min under Ar, the reaction was quenched with H2O, stirred for 30 min, concentrated in vacuo, diluted with EtOAc, washed with 5N HCl (100 mL) and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (0.5% MeOH/CH2Cl2) to give the title compound.

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