Water → HCID 58452777, compound

HRID 70587Notes

Reaction equation

HRID 70587 reaction equation
[OH2:1].[H-].C[O:4]CCO[Al+]OCCOC.[Na+].[H-].[Cl:16][C:17]1[C:18](=[O:38])[NH:19][C:20](/[C:23](/[C:30]2[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=2)=[CH:24]/[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][CH:22]=1>C1COCC1.CO>[Cl:16][C:17]1[C:18](=[O:38])[NH:19][C:20](/[C:23](/[C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:37])(=[O:4])=[O:1])=[CH:32][CH:31]=2)=[CH:24]/[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 58452414HCID 58452414, compound

Product 1

HCID 58452777HCID 58452777, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Water (3 mL) and Oxone(R) (853 mg) were sequentially added to a solution of 3-chloro-6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}pyridin-2(1H)-one obtained in Example 1-1 (160 mg) in THF-methanol (1:1, 6 mL), and the mixture was stirred at room temperature for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:hexane=10:0→9:1). The resulting crude product was recrystallized from a chloroform:ethyl acetate:hexane (1:1:1, 6 mL) solution to give the title compound as a colorless powder (130 mg, 74%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:hexane=10:0→9:1)
  7. customThe resulting crude product was recrystallized from a chloroform:ethyl acetate:hexane (1:1:1, 6 mL) solution

Sources & evidence

ORD record
ord-a556f9cc74d7401ab77f91387e02e919
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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