Potassium Carbonate → HCID 18679523, compound

HRID 1633664Notes

Reaction equation

HRID 1633664 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]#[C:23][CH2:24][CH2:25][CH2:26][OH:27])=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 186794765-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol

Product 1

HCID 18679523HCID 18679523, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

970 mg (2.6 mmol) 5-[1-(4-Trimethylsilanylethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol in 10 ml MeOH were treated with 41.4 mg (3 mmol) K2CO3. The solution was concentrated, the residue dissolved in ether and 0.5M HCl and the organic phase was washed with water and dried over Na2SO4. Column chromatography on silica gel with ether yielded 680 mg (87%) 5-[1-(4-Ethynyl-phenyl)-1H-indol-5-yl]-pent-4-yn-1-ol as orange oil, MS: 299 (M).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in ether
  3. wash0.5M HCl and the organic phase was washed with water
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d865e9172b944a3db7eca46594e8f725
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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