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

HRID 1275536Notes

Reaction equation

HRID 1275536 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+]>[CH2:11]1[O:21][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:13][CH2:12]1

Participants

4

Reactant 2

HCID 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 93%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

5-Fluoroindole (5.4 g, 0.04 mol), 1,4-cyclohexanedione monoethylene ketal (12.5 g, 0.08 mol) were placed in 60 ml of 2N potassium hydroxide methanolic solution. The reaction mixture were heated to reflux for 4 hours. The reaction was cooled and the product was isolated by filtration and washed with methanol to give 10.1 g (93%) of product as a white solid: mp 153-155° C.

Workup

  1. temperatureThe reaction mixture were heated
  2. temperatureto reflux for 4 hours
  3. temperatureThe reaction was cooled
  4. customthe product was isolated by filtration
  5. washwashed with methanol

Sources & evidence

ORD record
ord-cf5d86afbffa42fb9eaa69dec553e7f7
Source dataset
uspto-grants-2000_12
Patent number
US06162803

Reaction notes

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