Potassium Hydroxide → 3-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-fluoro-1H-indole

HRID 428483Notes

Reaction equation

HRID 428483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH2:11]1[O:21][C:14]2([CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)[O:13][CH2:12]1.[OH-].[K+]>CO>[O:13]1[C:14]2([CH2:19][CH2:18][C:17]([C:5]3[C:4]4[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:7][CH:6]=3)=[CH:16][CH2:15]2)[O:21][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 678615-FluoroindoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 105163803-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-fluoro-1H-indoleYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Fluoroindole (4.96 g, 0.036 mol), 1,4-cyclohexanedione monoethylene ketal (7.17 g, 0.046 mol) and potassium hydroxide (6 g, 91 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 8.59 g (86%) of product as a white solid: mp 153-155° C.

Workup

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

Sources & evidence

ORD record
ord-ffa2311badee405ebc69dae3b0454d87
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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