Sodium Chloride → 8-Benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl ether

HRID 1155568Notes

Reaction equation

HRID 1155568 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:20])[NH:7]2.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.[Cl-].[Na+]>O1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:13]([O:12][C:9]1[C:8]2[NH:7][C:6](=[O:20])[CH2:5][CH2:4][C:3]=2[C:2]([OH:1])=[CH:11][CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[O:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[O:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:20]1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 127517378-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 1317125618-Benzyloxy-3,4-dihydrocarbostyril-5-ol tetrahydropyranyl etherYield 112.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10 g of 5-hydroxy-8-benzyloxy-3,4-dihydrocarbostyril was dissolved in 100 ml of anhydrous tetrahydrofuran, and 100 mg of p-toluenesulfonic acid was added to the solution. 10 g of dihydropyran was slowly added dropwise thereto at room temperature while stirring. After completion of the addition, the mixture was stirred at room temperature for 12 hours, poured into a large volume of a saturated aqueous solution of sodium chloride and then extracted with chloroform. The extract was washed successively with a 5% aqueous solution of sodium hydroxide and water, and the chloroform layer dried over anhydrous potassium carbonate. The chloroform was evaporated under reduced pressure, and the residue was crystallized from petroleum ether. Recrystallization from ethanol-water afforded 9.5 g of 8-benzyloxy-3,4-dihydrocarbostyril-5-ol-tetrahydropyranyl ether (IV) as colorless needle-like crystals having a melting point of 113.5°-114° C.

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at room temperature for 12 hours
  3. extractionextracted with chloroform
  4. washThe extract was washed successively with a 5% aqueous solution of sodium hydroxide and water
  5. dry with materialthe chloroform layer dried over anhydrous potassium carbonate
  6. customThe chloroform was evaporated under reduced pressure
  7. customthe residue was crystallized from petroleum ether
  8. customRecrystallization from ethanol-water

Sources & evidence

ORD record
ord-a049f7a14ee943449f8c793cc6081651
Source dataset
uspto-grants-1981_11
Patent number
US04302588

Reaction notes

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