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Potassium Carbonate → 2-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole

HRID 1534387
Notes
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Reaction equation

HRID 1534387 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33]Br)[CH:26]=1>CC(C)=O>[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33][O:1][C:2]2[CH:3]=[C:4]([C:8]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenolHCID 167329213-(3-Bromoprop-1-ynyl)pyridine hydrobromide

Product 1

HCID 191016422-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazoleYield 59.4%

Reagents, catalysts & solvents 1

HCID 180Acetone
Solvent

Procedure

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.25 g), potassium carbonate (0.28 g), 3-(3-pyridyl)prop2-yn-1-yl bromide hydrobromide (0.28 g) and acetone (5 ml) was stirred and heated to reflux for 17 hours. The mixture was cooled to ambient temperature, filtered and the filtrate was evaporated. The residue was purified by column chromatography eluting with hexane/ethyl acetate (1:1 v/v) to give 2-[1-[3-(3-(3-pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole as an oil (0.217 g, 59%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with hexane/ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-83bb1010f6ee4e92a6577f3c0fba8d93
Source dataset
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05089495

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes