Acetic Acid → HCID 19895670, compound

HRID 1073875Notes

Reaction equation

HRID 1073875 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1.C(O)(=O)C>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19895692HCID 19895692, compound

Product 1

HCID 19895670HCID 19895670, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.97 g of 2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1benzopyran were dissolved in 50 ml of ethanol and shaken at room temperature under a hydrogen atmosphere with 10% palladium-on-charcoal in the presence of 0.5 ml of acetic acid. After 24 hours the catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 1.4 g of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl) -2H-1-benzopyran together with mixed fractions containing this compound and starting material. The procedure described above was carried out on the mixed fractions to give 675 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl) -2H-1-benzopyran which was recrystallized from t-butyl methyl ether and then melted at 100-102° C.

Workup

  1. filtrationAfter 24 hours the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

Sources & evidence

ORD record
ord-64e28b4229114ddebdd6ee909e5e30ce
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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