Tetrahydrofuran → HCID 24997071, compound

HRID 2076371Notes

Reaction equation

HRID 2076371 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[Cl-].[Cl-].[Cl-].[Al+3].[CH2:16]([C:18]12[CH2:33][CH2:32][C:31](=O)[C:30]([CH3:35])=[C:29]1[C:28]1[CH:27]=[CH:26][C:25]3[NH:24][N:23]=[CH:22][C:21]=3[C:20]=1[CH2:19]2)[CH3:17]>C(OCC)C>[CH2:16]([C:18]12[CH2:33][CH2:32][CH2:31][C:30]([CH3:35])=[C:29]1[C:28]1[CH:27]=[CH:26][C:25]3[NH:24][N:23]=[CH:22][C:21]=3[C:20]=1[CH2:19]2)[CH3:17]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 6451240Aluminum(III) ChlorideHCID 9943262HCID 9943262, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 24997071HCID 24997071, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of lithium aluminum hydride in THF (1.0M, 0.26 mL, 0.26 mmol) was diluted with diethyl ether (2 mL) and solid aluminum trichloride (0.098 g, 0.74 mmol) was added in portions. To the resulting solution was added a suspension of 9a-ethyl-6-methyl-8,9,9a,10-tetrahydroindeno[2,1-e]indazol-7(3H)-one (0.027 g, 0.10 mmol) in diethyl ether (1.5 mL). After 23 minutes, the reaction was quenched by the addition of EtOAc (0.5 mL) followed by 2N hydrochloric acid (0.5 mL). The reaction mixture was partitioned between EtOAc and water and the organic phase was washed with brine and dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (elution with 1:3 EtOAc/hexanes) to give 9a-ethyl-6-methyl-3,7,8,9,9a,10-hexahydroindeno[2,1-e]indazole.

Workup

  1. additionwas added in portions
  2. additionTo the resulting solution was added
  3. customthe reaction was quenched by the addition of EtOAc (0.5 mL)
  4. customThe reaction mixture was partitioned between EtOAc and water
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was chromatographed on silica gel (elution with 1:3 EtOAc/hexanes)

Sources & evidence

ORD record
ord-439646236dc44ba5a6b8bd51412362ed
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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