Indole → 3-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indole

HRID 428482Notes

Reaction equation

HRID 428482 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:10]1[O:20][C:13]2([CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[O:12][CH2:11]1.[OH-].[K+]>CO>[O:12]1[C:13]2([CH2:18][CH2:17][C:16]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)=[CH:15][CH2:14]2)[O:20][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 798IndoleHCID 14797Potassium HydroxideHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 27638573-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)-1H-indoleYield 89.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Indole (4.69, 40 mmol), 1,4-cyclohexanedione monoethylene ketal (6.3 g, 40 mmol) and potassium hydroxide (13.2 g, 200 mmol) were heated to reflux in 70 ml methanol for 6 hours. The reaction was cooled and the product was isolated by filtration and washed with water to give 9.1 g (89%) of product.

Workup

  1. temperatureThe reaction was cooled
  2. customthe product was isolated by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-c231f3e905344f7da9cd7cae7f810718
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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