Tetrahydrofuran → HCID 61677242, compound

HRID 2281636Notes

Reaction equation

HRID 2281636 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[O:4].C1COCC1>CO.[OH-].[Na+].[NH4+].[Cl-]>[O:16]([CH2:15][CH2:14][N:9]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]=2[CH:7]=[CH:8]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 67087062HCID 67087062, compound

Product 1

HCID 61677242HCID 61677242, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

1-(2-Phenoxy-ethyl)-1H-indole-4-carboxylic acid methyl ester (185 mg, 0.626 mmol) is suspended in a mixture of MeOH (3 ml) and 2 M NaOH (2 ml). The suspension is stirred at room temperature for 2 hours, THF (1 ml) is added and the reaction is heated at 60° C. for 1 hour. The reaction is allowed to cool to room temperature and diluted with sat. NH4Cl solution (10 ml), extracted with EtOAc (10 ml×3), dried over MgSO4, and concentrated in vacuo to give the title compound; [M+H]+ 282

Workup

  1. temperaturethe reaction is heated at 60° C. for 1 hour
  2. temperatureto cool to room temperature
  3. extractionextracted with EtOAc (10 ml×3)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dcaf7e66e6348eca23f509815af3696
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

Loading…