Ethanol → HCID 22385850, compound

HRID 895160Notes

Reaction equation

HRID 895160 reaction equation
[C:1]1(=[O:6])[O:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10].C(O)C>CS(C)=O.O1CCCC1>[OH:5][CH2:4][CH2:3][CH2:2][C:1](=[O:6])[CH2:10][C:9]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 7302Gamma-ButyrolactoneHCID 95893-AcetylpyridineHCID 24758Sodium hydride

Product 1

HCID 22385850HCID 22385850, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of γ-butyrolactone (1.92 mL, 2.15 g, 25.0 mmol), 60% suspension of sodium hydride in mineral oil (300 mg, 7.50 mmol) and 3-acetylpyridine (551 μL, 606 mg, 5.00 mmol) in dimethylsulfoxyde (4 mL) and tetrahydrofuran (36 mL) was stirred overnight at 25° C. Ethanol (4 mL) was added to destroy excess sodium hydride and the reaction mixture was adsorbed on silica gel (10 g). Flash chromatography on silica gel (75 g), eluting with DCM/MeOH/NH4OH (96/4/1), gave 1.14 g of a yellow oil containing compound 3-A (0.62 g, 60%).

Workup

  1. customto destroy excess sodium hydride
  2. washFlash chromatography on silica gel (75 g), eluting with DCM/MeOH/NH4OH (96/4/1)

Sources & evidence

ORD record
ord-21afd5efda7a4fc392410a7b7bd7c452
Source dataset
uspto-grants-2005_07
Patent number
US06914069B2

Reaction notes

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