Potassium Carbonate → 1-Phenyl-2-(4-hydroxy-2-butenylthio)indole

HRID 127516Notes

Reaction equation

HRID 127516 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]2=[S:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25]#[C:26][CH2:27][OH:28]>CC(C)=O.C1C=CC=CC=1>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[S:16][CH2:24][CH:25]=[CH:26][CH2:27][OH:28])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2027752-Butyn-1-ol, 4-chloro-HCID 147096341-Phenylindoline-2-thione

Product 1

HCID 544806471-Phenyl-2-(4-hydroxy-2-butenylthio)indoleYield 107.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

To a solution of the product of the above (1)(2.2 g) in acetone (20 ml) are added potassium carbonate (1.54 g) and 4-chloro-2-butyn-1-ol (1.03 g). The mixture is stirred for 4 hours and filtered. The filtrate is condensed at below the room temperature. The oily residue is dissolved in benzene and evaporated at below the room temperature. Ether is added to the residue and then a 30% solution (1.5 ml) in methylamine in methanol on ice bath. The mixture is stirred for 30 minutes and after addition of ether, washed with ice-cooled 3 N-hydrochloric acid, water, an aqueous solution of sodium bicarbonate and water successively. The ether layer is dried and evaporated to give the title compound as an oil (3.1 g). The oil is chromatographed on a column of silica gel and eluted with hexane-benzene (1:10) benzene and ether-benzene (1:100) successively. The title compound is obtained as colorless oil.

Workup

  1. filtrationfiltered
  2. customcondensed at below the room temperature
  3. customevaporated at below the room temperature
  4. additionEther is added to the residue
  5. stirringThe mixture is stirred for 30 minutes
  6. additionafter addition of ether
  7. washwashed with ice-
  8. temperaturecooled 3 N-hydrochloric acid, water
  9. dry with materialThe ether layer is dried
  10. customevaporated

Sources & evidence

ORD record
ord-78be17838aca4ecbb0e97e87fb12b712
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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