Tetrahydrofuran → HCID 19372767, compound

HRID 129228Notes

Reaction equation

HRID 129228 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[C:12]([NH:15][CH:16]1[CH2:45][C:20]2=[CH:21][N:22]([S:27]([C:30]3[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][C:33]([CH:39]([CH3:41])[CH3:40])=[CH:32][C:31]=3[CH:42]([CH3:44])[CH3:43])(=[O:29])=[O:28])[C:23]3[CH:24]=[CH:25][CH:26]=[C:18]([C:19]=32)[C:17]1([OH:48])[CH:46]=[CH2:47])(=O)[CH3:13].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(O)C>[CH2:12]([NH:15][CH:16]1[CH2:45][C:20]2=[CH:21][N:22]([S:27]([C:30]3[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][C:33]([CH:39]([CH3:40])[CH3:41])=[CH:32][C:31]=3[CH:42]([CH3:44])[CH3:43])(=[O:28])=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[C:18]([C:19]=32)[C:17]1([OH:48])[CH:46]=[CH2:47])[CH3:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 19372796HCID 19372796, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 19372767HCID 19372767, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

LAH (5 equivalents) was allowed to react with a THF solution (14.3 ml) of 4-acetylamino-3,4-dihydro-5-hydroxy-1-(2,4,6-triisopropylphenylsulfonyl)-5-vinyl-5H-benz[cd]indole (750 mg, 1.43 mmol) and was refluxed for 3 hours to complete the reaction. Ethanol was added to the reaction mixture to inactivate the excess amount of LAH and was added aqueous solution of Na2SO4. The reaction mixture was subjected to extraction with ethyl acetate. The extract was washed with an aqueous saline solution and, then, dried (anhydrous Na2SO4) and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography, eluting with ethyl acetate to afford 275 mg (38%) of the title compound as an oily product.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customthe reaction
  3. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  4. washThe extract was washed with an aqueous saline solution
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-51fd980c216f401c992d471db289f121
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

Loading…