5-Indanol → Indole

HRID 1975040Notes

Reaction equation

HRID 1975040 reaction equation
C1N=C[N:3](C(N2C=NC=C2)=O)C=1.[CH2:13]1[C:21]2[C:16](=[CH:17][C:18](O)=[CH:19][CH:20]=2)C[CH2:14]1>CN(C=O)C>[NH:3]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

4

Reactant 2

HCID 151185-IndanolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 798IndoleYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of CDI in 25 mL anhydrous DMF was added 1 (0.76 g, 1.72 mmol), see Example 4, in one portion. The mixture was allowed to stir at room temperature for 15 minutes, then at 80° C. for 2 hours. The solution was then cooled to room temperature, the 5-indanol added, and stirring continued for 16 hours. The reaction was quenched by pouring into 200 mL H2O, and the resulting yellow precipitate filtered and air dried. Column chromatography (30% EtOAc/Hex→50% EtOAc/Hex) yielded 0.24 g (25%) of 2, mp 258°-260° C.

Workup

  1. waitat 80° C. for 2 hours
  2. temperatureThe solution was then cooled to room temperature
  3. stirringstirring
  4. waitcontinued for 16 hours
  5. customThe reaction was quenched
  6. additionby pouring into 200 mL H2O
  7. filtrationthe resulting yellow precipitate filtered
  8. customair dried

Sources & evidence

ORD record
ord-666317ad422544ef921e71cad8d68191
Source dataset
uspto-grants-1994_02
Patent number
US05284862

Reaction notes

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