Sodium Hydroxide → HCID 54119850, compound

HRID 359368Notes

Reaction equation

HRID 359368 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[O:3]1.[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[N:11].[OH-].[Na+]>C(O)C.[Cl-].[Na+]>[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH:8]=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)[O:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 660424-CyanobenzaldehydeHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 54119850HCID 54119850, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of 2,2,5-trimethyl-3(2H)-furanone (1.5 g, 11.9 mM), 4-cyanobenzaldehyde (1.7 g, 13.1 mM) and 1N aqueous sodium hydroxide (1.2 mL, 1.2 mM) in ethanol (50 mL) was stirred 24 hours at room temperature. The reaction mixture was diluted with saturated aqueous sodium chloride (200 mL) and extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow solid. The crude product was purified by column chromatography (silica gel, 9:1, hexane-ethyl acetate) to afford pale yellow crystals (1.5 g, 53% yield), m.p. 169.5°-170.5° C.

Workup

  1. extractionextracted with diethyl ether (3×100 mL)
  2. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow solid
  7. customThe crude product was purified by column chromatography (silica gel, 9:1, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2b3a3183042a4045b2b51dcd5f67e44b
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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