Pyridine → HCID 20185253, compound

HRID 2309409Notes

Reaction equation

HRID 2309409 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=1)=[C:5]2C.[C:21](Cl)(=[O:23])[CH3:22].N1C=CC=C[CH:26]=1>>[C:21]([O:1][C:2]1([CH3:26])[CH:10]=[CH:9][C:8]2[C:4]([CH:5]=[C:6]([C:11]3[CH:12]=[C:13]([CH3:19])[C:14]([OH:18])=[C:15]([CH3:17])[CH:16]=3)[N:7]=2)=[CH:3]1)(=[O:23])[CH3:22]

Participants

4

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 13938646HCID 13938646, compound

Product 1

HCID 20185253HCID 20185253, compound

Conditions

Temperature
40 °C

Procedure

0.8 g of 5-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole was dissolved in 4 ml of pyridine, and under ice cooling, 0.26 g of acetyl chloride was added. The mixture was stirred at 40° C. for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, 2N hydrochloric acid and water, and purified by silica gel column chromatography to give 5-acetyloxy-2-(4-hydroxy-3,5-dimethylphenyl)-5-methylindole.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, 2N hydrochloric acid and water
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a50f76dff7e446699584f65dd1dce972
Source dataset
uspto-grants-1987_09
Patent number
US04695581

Reaction notes

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