Reacción #1463476

Ecuación de reacción

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

Rendimiento 67.4%

Disolventes

ethanol

toluene

toluene

toluene

Condiciones de reacción

Tratamiento posterior

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
   ExtracciónThe organic phase was extracted twice with water
4. 4
   ExtracciónThe aqueous phase was extracted twice with ether
5. 5
   Secadodried over magnesium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Otrothe filtrate was evaporated
8. 8
   OtroThe residue was purified on silica gel (5% ethyl acetate/cyclohexane)

Procedimiento

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.

Fuente