Water → HCID 22267208, compound

HRID 488868Notes

Reaction equation

HRID 488868 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=O.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CN(C=O)C>[CH3:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[C:3]2[CH:4]=[C:5]3[C:9]([CH2:8][CH2:7][CH2:6]3)=[CH:10][C:2]=2[O:1][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 10399965HCID 10399965, compound

Product 1

HCID 22267208HCID 22267208, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (6-hydroxy-2,3-dihydro-1H-inden-5-yl)(2-methylphenyl)methanone (2.0 g) in DMF (50 ml) was combined with sodium hydride (60%, in oil) (400 mg) with cooling in ice. After stirring at the same temperature for 30 minutes, the mixture was combined with ethyl bromoacetate (1 ml), and stirred for 1 hour. The reaction solution was combined with water and extracted with ethyl acetate. The extract was washed with water, and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in toluene (50 ml), and combined with DBU (2 ml). The reaction solution was heated under reflux overnight, and then combined with water, and extracted with ethyl acetate. The extract was washed with water, and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:3) to obtain a crude product of ethyl 3-(2-methylphenyl)-6,7-dihydro-5H-indeno[5,6-b]furan-2-carboxylate. The resultant crude product of ester was dissolved in a solvent mixture of THF (50 ml) and methanol (30 ml), combined with a 1 N solution of sodium hydroxide (30 ml), and stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the resultant residue was combined with water and extracted with ethyl acetate after acidifying with diluted hydrochloric acid. The extract was washed with water, and then dried over magnesium, and the solvent was distilled off under reduced pressure. The resultant residue was purified by recrystallization from ethyl acetate to obtain the title compound (0.9 g, yield: 39%) as a colorless crystal.

Workup

  1. temperaturewith cooling in ice
  2. stirringstirred for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. dissolutionThe resultant residue was dissolved in toluene (50 ml)
  8. temperatureThe reaction solution was heated
  9. temperatureunder reflux overnight
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water
  12. dry with materialdried over magnesium sulfate
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThe resultant residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:3)

Sources & evidence

ORD record
ord-48c5156b0bd2410ca2ecff0321daa7ec
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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