Sodium hydride → 5-(4-Ethyl-thiophen-2-ylmethoxy)-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 41681Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41681
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1)[CH3:2].[H-].[Na+].Cl[C:13]1[CH:21]2[CH:16]([CH:17]3[O:22][CH:20]2[CH2:19][CH2:18]3)[C:15](=[O:23])[CH:14]=1>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:8][O:9][C:13]2[CH:21]3[CH:16]([CH:17]4[O:22][CH:20]3[CH2:19][CH2:18]4)[C:15](=[O:23])[CH:14]=2)[S:6][CH:7]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 232612874-Ethyl-2-thiophenemethanolHCID 685678445-Chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Produkt 1

HCID 685700235-(4-Ethyl-thiophen-2-ylmethoxy)-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-oneAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (4-ethyl-thiophen-2-yl)methanol (369 mg, 2 mmol) in THF (10 ml) is added sodium hydride, 60% dispersion in mineral oil, (88 mg, 2.2 mmol) in one portion and the reaction stirred at room temp for 3 hours. The resulting dark yellow solution is then cooled to 0° C., and 5-Chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (341 mg, 2.4 mmol) is added and the resulting brown solution allowed to warm to ambient over 30 minutes, then stirred at room temp for 17 hours. Crude reaction is purified by flash chromatography to give 5-(4-ethyl-thiophen-2-ylmethoxy)-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one as a white solid (515 mg).

Aufarbeitung

  1. temperatureThe resulting dark yellow solution is then cooled to 0° C.
  2. temperatureto warm
  3. waitto ambient over 30 minutes
  4. stirringstirred at room temp for 17 hours
  5. customCrude reaction
  6. customis purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6690f8d29d5d4a94bbb1466d5090a09c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530667B2

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