Disodium 2,3-dihydroxybutanedioate → HCID 178520925, compound

Temperature

0 °C

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.

1. additionsubsequently added dropwise within 45 minutes to a solution
2. stirringAfter stirring at -50° C. for 2 hours the reaction mixture
3. extractionThe organic phase was extracted twice with water
4. extractionThe aqueous phase was extracted twice with ether
5. dry with materialdried over magnesium sulphate
6. filtrationfiltered
7. customthe filtrate was evaporated
8. customThe residue was purified on silica gel (5% ethyl acetate/cyclohexane)

ORD record

ord-f2b8ab4a5b7342778c871a769f79b8ae

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05662829