Sodium hydride → HCID 86661954, Verbindung

HRID 45903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45903
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86661954HCID 86661954, VerbindungAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2a6b0be894c1444eb83bc0ee1e8d8951
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541594B2

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