تفاعل #43281

معادلة التفاعل

TBSOTf

4

1-(4-Bromo-phenyl)-hexan-1-ol

2,6-lutidine

sodium bicarbonate

→

compound 5

المردود 88.4%

[1-(4-Bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane

المردود 88.4%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe resulting mixture was extracted with dichloromethane (30 mL)
2. 2
   غسيلthe dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL)
3. 3
   تجفيفThe dichloromethane solution was then dried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated
6. 6
   أخرىPurification of the residue by flash chromatography on silica gel (hexanes)

الإجراء التجريبي

TBSOTf (2.9 mL, 12.6 mmol) was added to an ice-cold solution of 4 (3.017 g, 11.7 mmol) and 2,6-lutidine (1.6 mL, 13.7 mmol) in dichloromethane (30 mL). The reaction was stirred for 2 h at room temperature and then 100 mL saturated sodium bicarbonate solution was added. The resulting mixture was extracted with dichloromethane (30 mL) and the dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL). The dichloromethane solution was then dried (MgSO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (hexanes) gave compound 5 (3.843 g, 88%).

المصدر