Acetyl chloride → HCID 19895658, compound

HRID 892513Notes

Reaction equation

HRID 892513 reaction equation
[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.[Cl-].[Al+3].[Cl-].[Cl-].[C:24](Cl)(=[O:26])[CH3:25].[OH-].[Na+]>[N+](C)([O-])=O>[C:24]([C:16]1[CH:17]=[CH:18][C:4]2[O:3][C:2]([CH3:19])([CH3:1])[CH2:7][CH:6]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=3)[C:5]=2[CH:15]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 19895670HCID 19895670, compound

Product 1

HCID 19895658HCID 19895658, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

712 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran were suspended in 10 ml of nitromethane at room temperature. 750 mg of aluminum chloride and then 500 mg of acetyl chloride were added. After 1 hour at room temperature dilute sodium hydroxide solution was added and the mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:3) and then ethyl acetate/ petroleum ether (1:1) for the elution. The resulting oil was triturated with n-hexane to give a solid which, after recrystallization from cyclohexane, yielded 165 mg of 6-acetyl-3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran of melting point 87°-88° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washethyl acetate/ petroleum ether (1:1) for the elution
  7. customThe resulting oil was triturated with n-hexane
  8. customto give a solid which
  9. customafter recrystallization from cyclohexane

Sources & evidence

ORD record
ord-2219091b7bdf4714adb475f3289ea184
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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