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

HRID 893326Notes

Reaction equation

HRID 893326 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>[CH2:10]1[O:20][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:12][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 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Indole (45.3 g, 0.38 mol), 1,4-cyclohexanedione monoethylene ketal (45.5 g, 0.29 mol) and potassium hydroxide (9.12 g, 0.16 mol) are heated to reflux in 100 mL of methanol for 18 hours. The reaction is cooled and the product is isolated by filtration and washed with water to give a white solid (69.0 g).

Workup

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

Sources & evidence

ORD record
ord-1c78870179004eeca3cdffaf12368bf7
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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