Acetic Anhydride → 10-Acetoxy-5,5-dimethyl-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

HRID 126797

Reaction equation

HRID 126797 reaction equation
[CH3:1][C:2]1([CH3:26])[C:21]2=[CH:22][CH:23]=[N:24][CH:25]=[C:20]2[C:5]2[C:6]([OH:19])=[CH:7][C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])=[CH:9][C:4]=2[O:3]1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:19][C:6]1[C:5]2[C:20]3[C:21]([C:2]([CH3:1])([CH3:26])[O:3][C:4]=2[CH:9]=[C:8]([CH:10]([CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11])[CH:7]=1)=[CH:22][CH:23]=[N:24][CH:25]=3)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 197814025,5-Dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

Product 1

HCID 2028784710-Acetoxy-5,5-dimethyl-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3.53 g. (0.01 mole) of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine, 1.22 g. (0.012 mole) of acetic anhydride, and 5 ml. of pyridine was stirred at room temperature for 24 hours. The reaction mixture was evaporated in vacuo, and the residue was taken up in ether. The ether solution was washed with water, dried with anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by chromatography on a Florosil® activated aluminum magnesium silicate 22 mm×30 inch column with chloroform to give the pure product.

Workup

  1. additionA mixture of 3.53 g
  2. customThe reaction mixture was evaporated in vacuo
  3. washThe ether solution was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on a Florosil® activated aluminum magnesium silicate 22 mm×30 inch column with chloroform
  7. customto give the pure product

Sources & evidence

ORD record
ord-088bf249f04d472f82e640deba12184c
Source dataset
uspto-grants-1981_03
Patent number
US04254116

Linked notes

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