Propargyl bromide → 2-[1-(3-(2-Propynyloxy)phenyl)-1-methoxypropyl]thiazole

HRID 1534386Notes

Reaction equation

HRID 1534386 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.[CH2:18](Br)[C:19]#[CH:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O: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:19]#[CH:18]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenol

Product 1

HCID 150499742-[1-(3-(2-Propynyloxy)phenyl)-1-methoxypropyl]thiazoleYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (31 g), 2-propynyl bromide (80% solution in toluene, 48.1 ml), potassium carbonate (48 g) and acetone (375 ml) was stirred and heated to reflux for 17 hours. The mixture was filtered and the filtrate was evaporated. The residue was partitioned between diethyl ether and water and the organic layer was washed with water, dried (MgSO4) and evaporated. The residue was purified by chromatography eluting with hexane/ethyl acetate (1:1 v/v) to give 2-[1-(3-(2-propynyloxy)phenyl)-1-methoxypropyl]thiazole as an oil (34 g, 94%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was partitioned between diethyl ether and water
  6. washthe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by chromatography
  10. washeluting with hexane/ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-075d7e67bd0f4a6db9be6d2f2680ef7f
Source dataset
uspto-grants-1992_02
Patent number
US05089495

Reaction notes

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