Sodium hydride → HCID 86661954, compound

HRID 45903Notes

Reaction equation

HRID 45903 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[CH:24]2[CH2:25][CH:21]([CH2:22][CH2:23]2)[C:20](=[O:26])[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[CH:24]4[CH2:25][CH:21]([CH2:22][CH2:23]4)[C:20](=[O:26])[CH:19]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57591516HCID 57591516, compoundHCID 59562443[2-(4-Chlorophenyl)selenazol-5-yl]methanol

Product 1

HCID 86661954HCID 86661954, compoundYield 63.7%

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) is added, in one portion, sodium hydride (60% dispersion in mineral oil, 44 mg, 1.1 mmol). The reaction mixture is stirred for 5 minutes at room temperature and 4-chlorobicyclo[3.2.1]oct-3-en-2-one (172 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, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]bicyclo[3.2.1]oct-3-en-2-one (275 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-2a6b0be894c1444eb83bc0ee1e8d8951
Source dataset
uspto-grants-2013_09
Patent number
US08541594B2

Reaction notes

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