تفاعل #46070

معادلة التفاعل

water

2,6-lutidine

alcohol

5-Bromo-2-methyl-2-pentanol

TBSOTf

→

9

المردود 80.0%

5-Bromo-2methyl-2[(tert-butyldimethylsilyl)oxy]-pentane

المردود 80.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted with CH2Cl2 (3×40 mL)
2. 2
   غسيلwere washed with 1N aqueous solution of NaOH (40 mL)
3. 3
   تجفيفdried (Na2SO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was purified by silica gel column chromatography (1% ethyl acetate/hexane)

الإجراء التجريبي

To a −50° C. cooled solution of alcohol 8 (3 g, 16.6 mmol) in anhydrous CH2Cl2 (50 mL) was added 2,6-lutidine (2.32 mL, 2.13 g, 19.89 mmol) followed by TBSOTf (4.57 mL, 5.26 g, 19.9 mmol). The solution was stirred at 0° C. for 15 min and water (10 mL) was added. The mixture was extracted with CH2Cl2 (3×40 mL), and combined organic phases were washed with 1N aqueous solution of NaOH (40 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (1% ethyl acetate/hexane) to give 3.9 g (13.2 mmol, 80%) of 9. 1H NMR (400 MHz, CDCl3) δ: 0.07 (6H, s), 0.85 (9H, s), 1.21 (6H, s), 1.55 (2H, m), 1.95 (2H, m),3.41 (2H, t, J=6.8 Hz)

المصدر