Water → HCID 23369618, compound

HRID 1900729Notes

Reaction equation

HRID 1900729 reaction equation
[OH:1][C:2]1[C:11]([CH2:12]/[CH:13]=[CH:14]/[CH2:15]O)=[CH:10][C:9]([CH3:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:18])[NH:7]2.B(F)(F)F.C(=O)(O)[O-].[Na+].O>ClCCCl>[CH3:17][C:9]1[CH:10]=[C:11]2[CH2:12][CH:13]([CH:14]=[CH2:15])[O:1][C:2]2=[C:3]2[C:8]=1[NH:7][C:6](=[O:18])[CH:5]=[CH:4]2

Participants

6

Reactant 4

HCID 962WaterHCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 23369676HCID 23369676, compound

Product 1

HCID 23369618HCID 23369618, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

5-Hydroxy-6-(trans-4-hydroxy-2-butenyl)-8-methylcarbostyril (2.6 g) was suspended in 1,2-dichloroethane (50 ml). Boron trifluoride.ether complex (7.5 ml) was added to the suspension, and the mixture was stirred at 60° C. for 5 hours. After the reaction, saturated sodium bicarbonate (50 ml) was added thereto, followed by stirring at room temperature for 1.5 hours. Water was added thereto and extraction was performed with chloroform. The extract was dried and condensed under reduced pressure, and the residue was recrystallized from a solvent mixture of chloroform-ether. As a result, 2.35 g of 5-methyl-2,3,6,7-tetrahydro-2-vinylfuro[2,3-f]quinoline-7-one was obtained as pale brown powdery crystals (97.6%).

Workup

  1. additionether complex (7.5 ml) was added to the suspension
  2. additionwas added
  3. stirringby stirring at room temperature for 1.5 hours
  4. extractionextraction
  5. customThe extract was dried
  6. customcondensed under reduced pressure
  7. customthe residue was recrystallized from a solvent mixture of chloroform-ether

Sources & evidence

ORD record
ord-55643ff315cc41719d032b79d254dfba
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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