Propargyl bromide → 2-[(Prop-2-yn-1-yl)sulfanyl]-1H-indole

HRID 127508Notes

Reaction equation

HRID 127508 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[S:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]#[CH:19]>CC(C)=O>[CH2:19]([S:10][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:18]#[CH:17]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 30323102-Indolinethione

Product 1

HCID 202847712-[(Prop-2-yn-1-yl)sulfanyl]-1H-indoleYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product (14.9 g) of the above (1) in acetone (250 ml) are added potassium carbonate (16.5 g) and propargyl bromide (14.3 g) successively and the mixture is stirred at room temperature for three hours. The precipitate is filtered off. The filtrate is condensed and extracted with ether after addition of water. The extract is washed with water, dried and evaporated to remove the solvent yielding an oily residue (23 g). The residue is chromatographed on a column of silica gel (100 g) and eluted with benzene-hexane. The eluate is condensed to give the tile compound as an oil (18.3 g). Yield: 98%

Workup

  1. filtrationThe precipitate is filtered off
  2. customcondensed
  3. extractionextracted with ether
  4. additionafter addition of water
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-6ef44c71cfa8464f8e6d519c2943171b
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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