Potassium Carbonate → 2-(4-Hydroxy-2-butynylthio)indole

HRID 127513Notes

Reaction equation

HRID 127513 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+].Cl[CH2:18][C:19]#[C:20][CH2:21][OH:22]>CC(C)=O>[OH:22][CH2:21][C:20]#[C:19][CH2:18][S:10][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2027752-Butyn-1-ol, 4-chloro-HCID 30323102-Indolinethione

Product 1

HCID 202847652-(4-Hydroxy-2-butynylthio)indoleYield 110.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-indolinthione (7.45 g) in acetone (75 ml) is added potassium carbonate (7.60 g). After stirring, 4-chloro-2-butyn-1-ol (5.48 g) is added thereto. The mixture is stirred at room temperature for 5 hours and filtered. The filtrate is condensed to remove the acetone completely. The residue is dissolved into diethylamine (10 ml), kept at room temperature for 1 hour and evaporated to remove the diethylamine aiming to remove excessive agents. The residue is dissolved in ether (250 ml), washed with water, 2 N hydrochloric acid, water and a saturated saline solution successively, dried and evaporated to give the title compound as an oil (12.0 g).

Workup

  1. stirringThe mixture is stirred at room temperature for 5 hours
  2. filtrationfiltered
  3. customcondensed
  4. customto remove the acetone completely
  5. dissolutionThe residue is dissolved into diethylamine (10 ml)
  6. customevaporated
  7. customto remove the diethylamine aiming
  8. customto remove excessive agents
  9. dissolutionThe residue is dissolved in ether (250 ml)
  10. washwashed with water, 2 N hydrochloric acid, water
  11. customa saturated saline solution successively, dried
  12. customevaporated

Sources & evidence

ORD record
ord-90b3b9c9d4a2437486afafb1e0eabcb7
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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