反应 #1463476

反应方程式

sodium tartrate

methyl trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexanecarboxylate

1-methylpiperazine

sodium bis(2-methoxyethoxy)-aluminum hydride

→

trans-4-(4-fluoro-cyclohex-3-enyl) cyclohexanecarbaldehyde

收率 67.4%

溶剂

ethanol

toluene

toluene

toluene

反应条件

后处理

1. 1
   workup.ADDITIONsubsequently added dropwise within 45 minutes to a solution
2. 2
   workup.STIRRINGAfter stirring at -50° C. for 2 hours the reaction mixture
3. 3
   萃取The organic phase was extracted twice with water
4. 4
   萃取The aqueous phase was extracted twice with ether
5. 5
   干燥dried over magnesium sulphate
6. 6
   过滤filtered
7. 7
   其他the filtrate was evaporated
8. 8
   其他The residue was purified on silica gel (5% ethyl acetate/cyclohexane)

实验过程

8.9 ml of sodium bis(2-methoxyethoxy)-aluminum hydride and 9 ml of toluene were cooled to 0° C. while gassing with nitrogen and treated within 30 minutes with a solution of 4.15 ml of 1-methylpiperazine in 20 ml of toluene. This solution was stirred at 0° C. for a further 30 minutes and subsequently added dropwise within 45 minutes to a solution, cooled to -50° C., of 3.0 g of methyl trans-4-(4-fluoro-cyclohex-3-enyl)cyclohexanecarboxylate in 40 ml of toluene. After stirring at -50° C. for 2 hours the reaction mixture was treated with 20 ml of ethanol and poured into a 10% sodium tartrate solution. The organic phase was extracted twice with water. The aqueous phase was extracted twice with ether and the organic phases were combined, dried over magnesium sulphate, filtered and the filtrate was evaporated. The residue was purified on silica gel (5% ethyl acetate/cyclohexane) and gave 1.77 g of trans-4-(4-fluoro-cyclohex-3-enyl) cyclohexanecarbaldehyde.

来源