Disodium 2,3-dihydroxybutanedioate → HCID 178520925, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence