Reaktion #218360

Reaktionsgleichung

3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

potassium hydroxide

ethyl acetate

dimethylthiocarbamoyl chloride

→

dimethyl-thiocarbamic acid O-(3-cyano-5,6,7,8-tetrahydro-naphthalene-2-yl) ester

Ausbeute 64.3%

Lösungsmittel

acetone

water

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was then stirred at room temperature for 16 h
2. 2
   WaschenThe organic layer was washed with saturated aqueous ammonium chloride, water, and brine
3. 3
   WaschenThe combined aqueous wash
4. 4
   Extraktionwas re-extracted with ethyl acetate
5. 5
   Trocknenthe organic washes were dried over magnesium sulfate
6. 6
   Sonstigeevaporated at reduced pressure
7. 7
   SonstigeThe crude oil was crystallized from ether/hexane

Vorschrift

To a solution of 3-hydroxy-5,6,7,8-tetrahydronaphthalene-2-carbonitrile prepared in method II-2 (3.00 g, 17.3 mmol) in acetone (60 mL) was added dropwise a solution of potassium hydroxide (1.07 g, 19.1 mmol, 1.1 eq) in water (40 mL) at 0° C. After stirring for 45 min, a solution of dimethylthiocarbamoyl chloride (2.35 g, 19.1 mmol, 1.1 eq) in acetone (40 mL) was added at 0° C. over 30 min. The reaction mixture was then stirred at room temperature for 16 h, and poured into ethyl acetate and water. The organic layer was washed with saturated aqueous ammonium chloride, water, and brine. The combined aqueous wash was re-extracted with ethyl acetate, and the organic washes were dried over magnesium sulfate and evaporated at reduced pressure. The crude oil was crystallized from ether/hexane to give dimethyl-thiocarbamic acid O-(3-cyano-5,6,7,8-tetrahydro-naphthalene-2-yl) ester (2.90 g, 64.3%) as a beige solid. 1H-NMR (Acetone-d6) δ 7.46 (s, 1H), 6.98 (s, 1H), 3.43 (d, J=4.2 Hz, 6H), 2.80 (m, 4H), 1.81 (m, 4H); MS ES (MH+=261). Rf=0.70 (30% ethyl acetate-hexane).

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