반응 #9069

반응 방정식

sodium potassium tartrate

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

DIBAL-H

→

title compound

수율 75.0%

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

수율 75.0%

용매

THF

THF

반응 조건

후처리

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

실험 절차

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).

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