Diethyl Ether → HCID 57803059, compound

HRID 2102657Notes

Reaction equation

HRID 2102657 reaction equation
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.CCOCC.[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18](=[O:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)([OH:24])[C:19](=[O:23])[NH:20]2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2413316-Chloroindoline-2,3-dioneHCID 178419650HCID 178419650, compound

Product 1

HCID 57803059HCID 57803059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclopentyl magnesium bromide in ether (2.0 M, 12.5 mL, 25 mmol) (Aldrich) was added dropwise to a suspension of 6-chloroisatin (1.82 g, 10 mmol) (prepared according to the procedure of Kraynack, E. A. et al., supra) in tetrahydrofuran (40 mL) under argon with cooling in a −25° C. bath and magnetic stirring at such a rate that reaction temperature was kept below −10° C. (approximately 30 minutes). Cooling bath was then removed and mixture allowed to warm to room temperature. After stirring for an additional 1 hour, 15% aqueous ammonium chloride solution (50 mL) was added and mixture extracted with ethyl acetate (2×75 mL). Ethyl acetate layers were then washed with water (75 mL), brine (75 mL), combined, dried (MgSO4), filtered and concentrated. Residue was stirred in dichloromethane (100 mL) at room temperature for 30 minutes and filtered to give crude rac-6-chloro-3-cyclopentyl-3-hydroxy-1,3-dihydro-indol-2-one as a white powder. (Yield 0.62 g, 24.6%).

Workup

  1. customprepared
  2. customthat reaction temperature
  3. customwas kept below −10° C.
  4. custom(approximately 30 minutes)
  5. temperatureCooling bath
  6. customwas then removed
  7. stirringAfter stirring for an additional 1 hour
  8. addition15% aqueous ammonium chloride solution (50 mL) was added
  9. extractionmixture extracted with ethyl acetate (2×75 mL)
  10. washEthyl acetate layers were then washed with water (75 mL), brine (75 mL)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated
  14. stirringResidue was stirred in dichloromethane (100 mL) at room temperature for 30 minutes
  15. filtrationfiltered

Sources & evidence

ORD record
ord-da54f0a5d46a4e388f78664db836d91d
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

Loading…