Sodium hydride → HCID 86637888, compound

HRID 2389312Notes

Reaction equation

HRID 2389312 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CS(O[CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=1)[O:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])(=O)=O>CN(C=O)C.CCOC(C)=O>[C:15]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[N:12]([CH2:28][CH2:29][CH2:30][O:31][C:32]3[CH:33]=[C:34]([CH:42]=[CH:43][CH:44]=3)[O:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[N:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 543237696-diphenylmethyl-3(2H)-pyridazinoneHCID 86637889HCID 86637889, compound

Product 1

HCID 86637888HCID 86637888, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(diphenylmethyl)pyridazin-3(2H)-one (158 mg) in DMF (2 mL) was added NaH (60% in oil, 26 mg) at 5° C. After stirring for an hour at ambient temperature, to the reaction mixture was added a solution of ethyl (3-{3-[(methylsulfonyl)oxy]propoxy}phenoxy)acetate (200 mg) in DMF (0.5 mL), and the resulting mixture was stirred at ambient temperature for 12 hours and then was stirred at 50° C. for 5 hours. After cooling, the reaction mixture was diluted with EtOAc (5 mL) and washed with water (5 mL) and brine (5 mL) two times. The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was purified by silica gel column chromatography (EtOAc:n-hexane=3:1) to give ethyl (3-{3-[3-(diphenylmethyl)-6-oxopyridazin-1(6H)-yl]propoxy}phenoxy)acetate (230 mg) as a pale yellow oil.

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 12 hours
  2. stirringwas stirred at 50° C. for 5 hours
  3. temperatureAfter cooling
  4. washwashed with water (5 mL) and brine (5 mL) two times
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give crude oil
  9. customThe crude oil was purified by silica gel column chromatography (EtOAc:n-hexane=3:1)

Sources & evidence

ORD record
ord-31b2effd29b742f998e7a4935bac60b5
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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