Isobutyraldehyde → HCID 67258953, compound

HRID 907772Notes

Reaction equation

HRID 907772 reaction equation
[CH:1](=[N:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][O:12][C:13]2=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](=O)[CH:20]([CH3:22])[CH3:21].[CH3:24][O-:25].[Na+]>C(OCC)(=O)CC>[CH:20]([CH:22]1[C:24](=[O:25])[C:10]2[C:14]([C:13]([O:12][CH3:11])=[O:18])=[CH:15][CH:16]=[CH:17][C:9]=2[NH:8][CH:1]1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 10942334Sodium MethoxideHCID 67258899HCID 67258899, compound

Product 1

HCID 67258953HCID 67258953, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

4-(benzylideneamino)isobenzofuran-1(3H)-one (237 mg, 1 mmol), isobutyraldehyde (216 mg, 3 mmol), sodium methanolate (162 mg, 3 mmol) and ethyl propionate (20 mL) were added and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1). 35 mg of solid methyl-3-isopropyl-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate was obtained. (yield: 11%). LC-MS (ESI) m/z: 308(M+1)+.

Workup

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1)

Sources & evidence

ORD record
ord-58a358cf10ea4f798eefb00a21daf9cd
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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