반응 #65638

반응 방정식

NH4Cl

8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

n-butyl lithium

3-chloromethyl-6-bromopyridine

→

title compound

수율 80.7%

10-[(2-bromo-5-pyridinyl)methyl]-8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine

수율 80.7%

용매

THF

hexane

THF

반응 조건

후처리

1. 1
   workup.WAITAfter 30 minutes
2. 2
   workup.WAITAfter 30 minutes
3. 3
   추출the mixture was extracted with ether
4. 4
   추출The organic extract
5. 5
   건조was dried over MgSO4
6. 6
   농축concentrated
7. 7
   기타The residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant

실험 절차

To a stirred solution of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine (2 g) in THF (25 mL) at -78° C. was added 1.6 M hexane solution of n-butyl lithium (5.4 mL). After 25 minutes, 3-chloromethyl-6-bromopyridine (1.79 g) in THF (5 mL) was added. After 30 minutes, the temperature was raised to -23° C. After 30 minutes, an excess saturated solution of NH4Cl was added and the mixture was extracted with ether. The organic extract was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel using 10% ethyl acetate in hexane as eluant. Appropriate fractions were pooled to give the title compound (2.8 g) as a thick gum.

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