Sodium hydride → 2,3,4,5-Tetrahydro-1-benzoxepine

HRID 1723046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723046
[H-].[Na+].S(O[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+].O.O>[O:20]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:16][CH2:15][CH2:14][CH2:19]1

Komponenten

7

Edukt 2

HCID 24758Sodium hydrideHCID 17221462-Hydroxyphenyl 4-methylbenzenesulfonate

Produkt 1

HCID 225522,3,4,5-Tetrahydro-1-benzoxepine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a mixture of 18.22 g of sodium hydride (60% dispersed in mineral oil) and 200 ml THF is added dropwise at 0° C. a solution of 146 g of o-tosyloxyphenol in 100 ml of THF. The reaction mixture is allowed to come to room temperature overnight. The reaction mixture is then chilled and 20 ml of H2O is added slowly. The mixture is then diluted with ethyl acetate and with brine and water. The organic layer is dried (MgSO4), filtered, and concentrated purification by flash column chromatography affords 2,3,4,5-tetrahydro-1-benzoxepin.

Aufarbeitung

  1. temperatureThe reaction mixture is then chilled
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8732e9b3facf4ddfacd780301e351695
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04859683

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