تفاعل #9067

معادلة التفاعل

methyl-4-(oxazol-2-yl)-benzoate

DIBAL-H

→

alcohol

المردود 89.0%

4-(oxazol-2-yl)-benzyl alcohol

المردود 89.0%

المذيبات

CH2Cl2

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىthen quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL)
2. 2
   أخرىThe phases were separated
3. 3
   استخلاصthe aqueous layer extracted with CH2Cl2 (3×10 mL)
4. 4
   تجفيفThe combined organic fractions were dried (Na2SO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىpurified by chromatography on silica gel (10:1 CH2Cl2/MeOH)

الإجراء التجريبي

To a solution of methyl-4-(oxazol-2-yl)-benzoate (0.203 g, 1 mmol) in CH2Cl2 (10 mL) 0° C. was added DIBAL-H (4 mL of a 1.0M solution in dichloromethane, 4 mmol) over 10 minutes. The resultant solution was stirred at 0° C. for 2 hours then quenched with an aqueous saturated solution of sodium potassium tartrate (20 mL) and the biphasic mixture stirred rapidly for 60 minutes. The phases were separated and the aqueous layer extracted with CH2Cl2 (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered, concentrated and purified by chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title alcohol (0.156 g, 89%). 1H NMR (CDCl3) δ 3.42 (t, 1H, J=6.0 Hz (OH)), 4.77 (s, 2H, J=6.0 Hz), 7.24 (s, 1H), 7.47 (d, 2H, J=7.8 Hz), 7.71 (s, 1H), 8.05 (d, 2H, J=7.8 Hz).

المصدر