تفاعل #9906

معادلة التفاعل

6-cyclohexylidene-hexanoic acid methyl ester

DIBAL-H

→

6-cyclohexylidene-hexan-1-ol

المردود 100.7%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction was quenched by MeOH (5 mL)
2. 2
   workup.ADDITIONSaturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture
3. 3
   workup.WAITAfter string for 1 h
4. 4
   أخرىthe organic layer was separated
5. 5
   استخلاصthe aqueous phase was extracted with ether
6. 6
   غسيلThe combined organic layers were washed with water and brine
7. 7
   أخرىdried
8. 8
   أخرىEvaporation of the solvent

الإجراء التجريبي

To a stired solution of 6-cyclohexylidene-hexanoic acid methyl ester (1.28 g, 6.10 mmol) in toluene (60 mL) was added DIBAL-H (15.3 mL, 1 M solution in hexane, 15.3 mmol) dropwise at 0° C. under N2. After stirring at 0° C. for 30 min, the reaction was quenched by MeOH (5 mL). Saturated aqueous sodium potassium tartrate (40 mL) was added to the reaction mixture. After string for 1 h, the organic layer was separated and the aqueous phase was extracted with ether. The combined organic layers were washed with water and brine and dried. Evaporation of the solvent gave 6-cyclohexylidene-hexan-1-ol (1.12 g, 100%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.05 (1H, m), 3.62 (2H, t, J=6.6 Hz), 2.05 (6H, m), 1.42–1.64 (8H, m), 1.34 (2H, m); 13C NMR (75 MHz, CDCl3) δ 139.78, 121.25, 63.22, 37.43, 32.96, 30.22, 28.96, 28.11, 27.23, 25.58.

المصدر