Benzaldehyde → HCID 18182388, compound

HRID 1359401Notes

Reaction equation

HRID 1359401 reaction equation
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[C:16]1([C:22]2[N:23]=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O.O1CCCC1.CCCCCC>[OH:37][CH:30]([C:26]1[CH:27]=[C:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:23]=[N:24][C:25]=1[O:28][CH3:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 130352,2,6,6-TetramethylpiperidineHCID 110845673-methoxy-6-phenylpyridazineHCID 178418339Butyllithium

Product 1

HCID 18182388HCID 18182388, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

7,7 ml of a hexane solution containing 1.52 mol of normal butyllithium was slowly added dropwise into a solution of 50 ml of tetrahydrofuran containing 2.0 ml of 2,2,6,6-tetramethylpiperidine under ice-cooling. After stirring for one hour under ice-cooling, it was cooled to −78° C. and 10 ml of a tetrahydrofuran solution containing 1.68 g of 3-phenyl-6-methoxypyridazine was slowly added dropwise thereinto. After stirirng at −78° C. for 2 hours, benzaldehyde was slowly added dropwise thereinto. After stirring at −78° C. for further 30 minutes, it was stirred at room temperature overnight. Water was added to the reaction solution, extracted with ethyl acetate and the organic phase was washed with brine. After removing the solvent, the residue was subjected to NH-silica gel (Fuji Silicia) chromatography and eluted with hexane/ethyl acetate (3:1) and then with hexane/ethyl acetate (1:1), to give 1.39 g of the target compound.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionwas slowly added dropwise
  4. waitAfter stirirng at −78° C. for 2 hours
  5. stirringAfter stirring at −78° C. for further 30 minutes
  6. stirringit was stirred at room temperature overnight
  7. extractionextracted with ethyl acetate
  8. washthe organic phase was washed with brine
  9. customAfter removing the solvent
  10. washeluted with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-21e35db1e5344a9db94d1448725fa369
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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