Sodium hydride → HCID 66742459, compound

HRID 45908Notes

Reaction equation

HRID 45908 reaction equation
[Cl: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)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:19]1[CH:25]2[CH2:26][CH:22]([CH2:23][CH2:24]2)[C:21](=[O:27])[CH:20]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:19]3[CH:25]4[CH2:26][CH:22]([CH2:23][CH2:24]4)[C:21](=[O:27])[CH:20]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57591516HCID 57591516, compoundHCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol

Product 1

HCID 66742459HCID 66742459, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol (1.1 g, 4.6 mmol) in anhydrous tetrahydrofuran (20 ml) is added, in one portion, sodium hydride (60% dispersion in mineral oil, 184 mg, 4.6 mmol). The reaction mixture is stirred for 5 minutes at room temperature and 4-chlorobicyclo[3.2.1]oct-3-en-2-one (720 mg, 4.6 mmol) is added in one portion. The reaction mixture is stirred at room temperature overnight. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}bicyclo[3.2.1]oct-3-en-2-one (1.24 g)

Workup

  1. stirringThe reaction mixture is stirred at room temperature overnight
  2. additionSilica gel is added to the crude
  3. customreaction mixture
  4. customthe solvent is evaporated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-994e3f73ffd042758d1c8616164dfd90
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

Loading…