Dimethylformamide → HCID 20287836, compound

HRID 126827Notes

Reaction equation

HRID 126827 reaction equation
CI.[CH3:3][C:4]1([CH3:28])[C:23]2=[CH:24][CH:25]=[N:26][CH:27]=[C:22]2[C:7]2[C:8]([OH:21])=[CH:9][C:10]([CH:12]([CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13])=[CH:11][C:6]=2[O:5]1.[CH3:29]N(C)C=O.C[O-].[Na+]>O>[CH3:28][C:4]1([CH3:3])[C:23]2=[CH:24][CH:25]=[N:26][CH:27]=[C:22]2[C:7]2[C:8]([O:21][CH3:29])=[CH:9][C:10]([CH:12]([CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:13])=[CH:11][C:6]=2[O:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 197814025,5-Dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano[3,4-d]pyridine

Product 1

HCID 20287836HCID 20287836, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl iodide (5.11 g., 0.036 mole) was added dropwise to a stirred solution of 10.59 g. (0.03 mole) of 5,5-dimethyl-10-hydroxy-8-(3-methyl-2-octyl)-5H-[1]benzopyrano [3,4-d]pyridine in 300 ml. of N,N-dimethylformamide containing 1.78 g. (0.033 mole) of sodium methoxide. The mixture was stirred at room temperature for 18 hours and 300 ml. of water was added and extracted with petroleum ether (30°-60°). The combined petroleum ether extracts were washed with water, dried with anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by chromatography on a Florisil® column with chloroform or by distillation under reduced pressure to give the pure product.

Workup

  1. extractionextracted with petroleum ether (30°-60°)
  2. washThe combined petroleum ether extracts were washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. distillationThe residue was purified by chromatography on a Florisil® column with chloroform or by distillation under reduced pressure
  6. customto give the pure product

Sources & evidence

ORD record
ord-225fd7f50b8b4f368035519e5647a375
Source dataset
uspto-grants-1981_03
Patent number
US04254116

Reaction notes

Loading…