反応 #218360

反応方程式

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

収率 64.3%

溶媒

acetone

water

water

acetone

反応条件

後処理

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

実験手順

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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