Реакция #1755468

Уравнение реакции

86

(4-Prop-2-ynyl-cyclohexyl)-methanol

pyridine

acetic anhydride

→

87

Выход 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

Выход 91.4%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.WAITAfter 16 hours
2. 2
   ТемператураThe reaction mixture was heated at 75° C. for 3 hours
3. 3
   ДругоеThe solvent was removed under reduced pressure
4. 4
   Другоеto yield a yellow oil which
5. 5
   Другоеwas purified by flash chromatography, on silica gel
6. 6
   Промывкаeluting with 1:3 ether/petroleum ether

Методика

To a solution of 960 mg (6.31 mmol) of 86 in 6 mL DMF was added 0.62 mL (7.57 mmol) pyridine and 0.78 mL (8.27 mmol) acetic anhydride. The reaction was allowed to stir overnight at room temperature. After 16 hours, starting material still remained. The reaction mixture was heated at 75° C. for 3 hours. The solvent was removed under reduced pressure to yield a yellow oil which was purified by flash chromatography, on silica gel, eluting with 1:3 ether/petroleum ether to yield 1.12 g (91%) of 87 as an oil. 1H NMR (CDCl3) δ3.87 (d, J=6.2 Hz, 2H), 2.06 (d, J=4.3 Hz, 2H), 2.03 (s, 3H), 1.98-1.93 (m, 1H), 1.92-1.83 (m, 2H), 1.83-1.74 (m, 2H), 1.63-1.36 (m, 2H), 1.12-0.90 (m, 4H); 13C NMR (CDCl3) δ 171.7, 83.7, 69.9, 69.6, 37.4, 37.3, 32.1, 29.7, 26.5, 21.4; APCI m/z (rel intensity) 195 (M+, 30), 153 (M+, 70), 135 (M+, 100).

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