1-Bromohexane → HCID 18973570, compound

HRID 2394416Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[CH2:12]([N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 55 °C

Procedure

There were dissolved, in 26 ml of dimethylformamide, 2.00 g of indole-4-carbaldehyde and 4.64 g of n-hexyl bromide, followed by addition of 9.52 g of potassium carbonate and heating the reaction solution to 55° C. with stirring for 12.5 hours. The reaction solution was poured into 500 ml of a 10% aqueous solution of ammonium chloride followed by extraction with ethyl acetate (150 ml×3). The resulting organic phase was washed with a saturated common salt solution, dried over anhydrous sodium sulfate, followed by removal of the solvent through evaporation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1.91 g of 1-hexylindole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 61%.

Workup

extractionfollowed by extraction with ethyl acetate (150 ml×3)
washThe resulting organic phase was washed with a saturated common salt solution
dry with materialdried over anhydrous sodium sulfate
customfollowed by removal of the solvent through evaporation under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-2b56548b01c340f993ea47f71cbe2179
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811439

Reaction notes

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