Triglyme → 5-{1-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41673

Reaction equation

HRID 41673 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([OH:15])[CH3:14])=[CH:11][N:12]=2)=[C:4]([CH3:16])[CH:3]=1.Cl[C:18]1[CH:26]2[CH:21]([CH:22]3[O:27][CH:25]2[CH2:24][CH2:23]3)[C:20](=[O:28])[CH:19]=1.[H-].[Na+].COCCOCCOCCOC>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:18]3[CH:26]4[CH:21]([CH:22]5[O:27][CH:25]4[CH2:24][CH2:23]5)[C:20](=[O:28])[CH:19]=3)[CH3:14])=[CH:11][N:12]=2)=[C:4]([CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 8189TriglymeHCID 24758Sodium hydrideHCID 595846761-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanolHCID 685678445-Chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Product 1

HCID 687735855-{1-[2-(4-Bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-oneYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol (450 mg, 1.5 mmol) and 5-chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (277 mg, 1.5 mmol) in tetrahydrofuran (10 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 60 mg, 1.5 mmol). The reaction mixture is stirred at room temperature for 24 hours. The crude reaction mixture is vacced down under reduced pressure and 10 ml of triglyme are added. The reaction mixture is therefore heated to reflux for 30 minutes. The crude reaction mixture is vacced down and purified by flash chromatography on silica gel to give a yellow solid. The solid is washed with iso-hexane to give 5-{1-[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (490 mg).

Workup

  1. customThe crude reaction mixture
  2. additionare added
  3. temperatureThe reaction mixture is therefore heated
  4. temperatureto reflux for 30 minutes
  5. customThe crude reaction mixture
  6. custompurified by flash chromatography on silica gel
  7. customto give a yellow solid
  8. washThe solid is washed with iso-hexane

Sources & evidence

ORD record
ord-d1656d9515194173a1d6413fd2f90966
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Linked notes

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