Réaction #1755468

Équation de réaction

86

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

pyridine

acetic anhydride

→

87

Rendement 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

Rendement 91.4%

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source