HCID 53833634, compound → HCID 54429984, compound

HRID 582045Notes

Reaction equation

HRID 582045 reaction equation
ClC1C=CC(C2(C3C=CC(Cl)=CC=3)[O:12][C:11]3[CH:13]=[CH:14][C:15]([CH2:17][C:18]([C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:22]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:21]=4)=[O:19])=[CH:16][C:10]=3[O:9]2)=CC=1>C(O)(=O)C.O>[OH:9][C:10]1[CH:16]=[C:15]([CH2:17][C:18]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:21]=2)=[O:19])[CH:14]=[CH:13][C:11]=1[OH:12]

Participants

3

Reactant 1

HCID 53833634HCID 53833634, compound

Product 1

HCID 54429984HCID 54429984, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

Ethyl 4-(3-[(2,2-di[4-chlorophenyl]-1,3-benzodioxolan-5-yl)methylcarbonyl]indol-1-yl)butanoate (9.5 g) (see Preparation 9) was dissolved in acetic acid/water (9:1) (100 ml) and heated under reflux for one hour. The reaction mixture was cooled, evaporated to dryness and partitioned between ethyl acetate and brine. The organic layer was separated, dried (MgSO4) and evaporated to a brown oil. Flash chromatography (silica, eluant=10:1 dichloromethane/ethanol) gave the title compound as a pale tan solid (4.5 g). LRMS m/z=382 (m+1)+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. temperatureThe reaction mixture was cooled
  4. customevaporated to dryness
  5. custompartitioned between ethyl acetate and brine
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated to a brown oil

Sources & evidence

ORD record
ord-fc886b9fbf224544a455131deda26772
Source dataset
uspto-grants-1999_07
Patent number
US05922747

Reaction notes

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