Diisopropyl Ether → HCID 22449323, compound

HRID 2187036Notes

Reaction equation

HRID 2187036 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].Br[CH:17]([CH3:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(OC(C)C)(C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH2:22]([O:21][C:19]([CH2:18][CH2:17][CH2:24][C:3]12[CH2:12][CH2:11][CH2:10][C:5]3[C:4]1=[C:9]([CH:8]=[CH:7][CH:6]=3)[NH:1][C:2]2=[O:13])=[O:20])[CH3:23]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 95424Butanoic acid, 3-bromo-, ethyl esterHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

Product 1

HCID 22449323HCID 22449323, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(RS)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (8.65 g, 50 mmol) was dissolved in anhydrous N,N,-dimethylformamide (70 ml). Then, 60% sodium hydride (2.0 g, 50 mmol) was added thereto and the resulting mixture was stirred at room temperature for 1 hour. Successively the reaction mixture obtained was cooled to −20° C., and ethyl 3-bromobutyrate (7.15 ml, 50 mmol) was added thereto. The resulting mixture was stirred at room temperature for further 18 hours. Ethyl acetate and water were added thereto to extract a reaction product. The ethyl acetate solution was washed with saturated saline solution and then dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain a reaction product. Thereafter, diisopropyl ether was added to the resulting reaction product to crystallized the same. Thus, the above-described object compound was obtained in an amount of 8.01 g (yield 56%).

Workup

  1. customSuccessively the reaction mixture obtained
  2. temperaturewas cooled to −20° C.
  3. stirringThe resulting mixture was stirred at room temperature for further 18 hours
  4. extractionto extract a reaction product
  5. washThe ethyl acetate solution was washed with saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customto obtain a reaction product
  9. customto crystallized the same
  10. customThus, the above-described object compound was obtained in an amount of 8.01 g (yield 56%)

Sources & evidence

ORD record
ord-c86919a480354592a9bb668b0ff6d4e7
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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