Sodium hydride → HCID 66742678, compound

HRID 45904Notes

Reaction equation

HRID 45904 reaction equation
[Br:1][C:2]1[S:3][C:4]([CH2:7][OH:8])=[CH:5][N:6]=1.Cl[C:10]1[CH:16]2[CH2:17][CH:13]([CH2:14][CH2:15]2)[C:12](=[O:18])[CH:11]=1.[H-].[Na+]>O1CCCC1>[Br:1][C:2]1[S:3][C:4]([CH2:7][O:8][C:10]2[CH:16]3[CH2:17][CH:13]([CH2:14][CH2:15]3)[C:12](=[O:18])[CH:11]=2)=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 7213124(2-Bromo-1,3-thiazol-5-yl)methanolHCID 57591516HCID 57591516, compound

Product 1

HCID 66742678HCID 66742678, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-bromothiazol-5-yl)methanol (4.85 g, 25 mmol) and 4-chloro-bicyclo[3.2.1]oct-3-en-2-one (3.92 g, 25 mmol) in anhydrous tetrahydrofuran (100 ml) is added, in small portions, sodium hydride (60% dispersion in oil, 1.00 g, 25 mmol) at 0° C. The reaction mixture is stirred overnight and allowed to warm to room temperature. 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-(2-bromothiazol-5-ylmethoxy)bicyclo[3.2.1]oct-3-en-2-one (6.43 g)

Workup

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-969395d855b04c7fbb15e86f4ffde491
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

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