تفاعل #9069

معادلة التفاعل

sodium potassium tartrate

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

DIBAL-H

→

title compound

المردود 75.0%

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

المردود 75.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe biphasic mixture stirred rapidly for 60 min
2. 2
   أخرىThe phases were separated
3. 3
   استخلاصthe aqueous layer extracted with ether (3×20 mL)
4. 4
   تجفيفThe combined organic fractions were dried (Na2SO4)
5. 5
   تركيزconcentrated
6. 6
   أخرىpurified by column chromatography on silica gel (10:1 CH2Cl2/MeOH)

الإجراء التجريبي

To a 0° C. solution of methyl-4-(benzothiazol-2-yl)-benzoate (prepared as described by A. Brembilla, D. Roizard and P. Lochon Synth. Commun. 1990, 20, 3379) (1.08 g, 4 mmol) in THF (20 mL) was added DIBAL-H (20 mL of a 1.0M solution in THF, 20 mmol) over 10 minutes. The resulting solution was stirred at 0° C. for 2 hours, then an aqueous saturated solution of sodium potassium tartrate was added and the biphasic mixture stirred rapidly for 60 min. The phases were separated and the aqueous layer extracted with ether (3×20 mL). The combined organic fractions were dried (Na2SO4), concentrated and purified by column chromatography on silica gel (10:1 CH2Cl2/MeOH) to afford the title compound (0.69 g, 75%). 1H NMR (CD3OD) δ 4.69 (s, 2H), 7.43 (t, 1H, J=7.8 Hz), 7.53 (m, 3H), 7.99 (m, 1H), 8.06 (m, 3H).

المصدر