Sodium Chloride → 1-Methyl-8-benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl ether

HRID 1155569Notes

Reaction equation

HRID 1155569 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[NH:17][C:16](=[O:19])[CH2:15][CH2:14][C:13]=2[C:12]([OH:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1.[H-].[Na+].CI.[Cl-].[Na+]>CN(C)C=O>[CH3:22][N:17]1[C:18]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=[C:12]([OH:20])[C:13]=2[CH2:14][CH2:15][C:16]1=[O:19].[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1317125618-Benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl ether

Product 1

HCID 1317125621-Methyl-8-benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl etherYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 g of 8-benzyloxy-3,4-dihydrocarbostyril-5-ol-detrahydropyranyl ether (IV) was dissolved in 100 ml of anhydrous dimethylformamide, and 810 g of sodium hydride was slowly added to the solution while stirring, followed by stirring at room temperature for 1 hour. 1.05 ml of methyl iodide was further added dropwise thereto followed by stirring at the same temperature for 2 hours. The reaction mixture was poured into a large volume of a saturated aqueous solution of sodium chloride, extracted with chloroform, washed with water and dried over anhydrous potassium carbonate. The chloroform was evaporated under reduced pressure, and the residue was recrystallized from ligroin to obtain 1.42 g of 1-methyl-8-benzyloxy-3,4-dihydrocarbostyril-5-ol-tetrahydropyranyl ether as colorless needle-like crystals having a melting point of 110.5°-111.5° C.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. stirringby stirring at the same temperature for 2 hours
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe chloroform was evaporated under reduced pressure
  7. customthe residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-08a508042c14402b8282226a7e019029
Source dataset
uspto-grants-1981_11
Patent number
US04302588

Reaction notes

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