Sodium hydride → HCID 59562413, compound

HRID 1849968Notes

Reaction equation

HRID 1849968 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[Se:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:18]1[C:23]([CH3:25])([CH3:24])[O:22][C:21]([CH3:27])([CH3:26])[C:20](=[O:28])[CH:19]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[Se:9][C:10]([CH2:13][O:14][C:18]3[C:23]([CH3:24])([CH3:25])[O:22][C:21]([CH3:27])([CH3:26])[C:20](=[O:28])[CH:19]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59562418HCID 59562418, compoundHCID 59562443[2-(4-Chlorophenyl)selenazol-5-yl]methanol

Product 1

HCID 59562413HCID 59562413, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [2-(4-chlorophenyl)selenazol-5-yl]methanol (300 mg, 1.1 mmol) in dry tetrahydrofuran (5 ml) under an atmosphere of nitrogen is added, in one portion, the sodium hydride (44 mg, 1.1 mmol). The reaction mixture is stirred for 5 minutes at room temperature and 5-chloro-2,2,6,6-tetramethyl-6H-pyran-3-one (208 mg, 1.1 mmol) is added in one portion. 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 5-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]-2,2,6,6-tetramethyl-6H-pyran-3-one (261 mg).

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-04cf238d6575483ba3568925459b4f25
Source dataset
uspto-grants-2015_02
Patent number
US08956999B2

Reaction notes

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