Potassium Iodide → 2,3-Dihydro-4,7-dimethyl-5-[(2-methyl-2-propenyl)oxy]-1H-indole-1-carbaldehyde

HRID 985579Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:14])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([CH:12]=[O:13])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:24][C:25]([CH3:27])=[CH2:26]>CN(C)C=O.O>[CH3:14][C:3]1[C:2]([O:1][CH2:26][C:25]([CH3:27])=[CH2:24])=[CH:10][C:9]([CH3:11])=[C:8]2[C:4]=1[CH2:5][CH2:6][N:7]2[CH:12]=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

2,3-Dihydro-5-hydroxy-4,7-dimethyl-1H-indole-1-carbaldehyde (5.74 g, 30 mmol) was dissolved in N,N-dimethylformamide (100 ml) and to the solution were added potassium carbonate (8.29 g, 60 mmol), potassium iodide (0.50 g, 3 mmol) and 3-chloro-2-methyl-1-propene (4.41 ml, 45 mmol). The mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into cold water (300 ml), and extracted with ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel. (hexane:ethyl acetate=6:1) to obtain 6.00 g of the title compound.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over sodium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-889dec0651ec4b7ca502bb76c806e125
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872718B1

Reaction notes

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