Réaction #69959

Équation de réaction

5-Chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

(4-ethyl-thiophen-2-yl)methanol

sodium hydride

→

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

Rendement 88.7%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting dark yellow solution is then cooled to 0° C.
2. 2
   Températureto warm
3. 3
   workup.WAITto ambient over 30 minutes
4. 4
   workup.STIRRINGstirred at room temp for 17 hours
5. 5
   AutreCrude reaction
6. 6
   Autreis purified by flash chromatography

Mode opératoire

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).

Source