Reacción #1755468

Ecuación de reacción

86

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

pyridine

acetic anhydride

→

87

Rendimiento 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

Rendimiento 91.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente