Sodium hydride → HCID 59562509, compound

HRID 1849973Notes

Reaction equation

HRID 1849973 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.Cl[C:17]1[CH:23]2[O:24][C:20]([CH3:25])([CH2:21][CH2:22]2)[C:19](=[O:26])[CH:18]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH:13]([O:15][C:17]3[CH:23]4[O:24][C:20]([CH3:25])([CH2:21][CH2:22]4)[C:19](=[O:26])[CH:18]=3)[CH3:14])=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 595624751-[2-(4-Chlorophenyl)thiazol-5-yl]ethanolHCID 59562500HCID 59562500, compound

Product 1

HCID 59562509HCID 59562509, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol (129 mg, 0.54 mmol) and 4-chloro-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one (93 mg, 0.54 mmol) in dry THF (5 ml) is added in one portion the sodium hydride, 60% dispersion in mineral oil, (21 mg, 0.54 mmol). The reaction mixture is stirred at room temperature overnight. Silica gel is added to the crude reaction mixture, and the solvent is evaporated under reduced pressure. The residue is purified by flash chromatography on silica gel to give 4-{1-[2-(4-Chlorophenyl)thiazol-5-yl]-ethoxy}-1-methyl-8-oxabicyclo[3.2.1]oct-3-en-2-one (160 mg).

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-daee4efe7f49483fba35de961019f4d0
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

Loading…