Reaktion #1755468

Reaktionsgleichung

86

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

pyridine

acetic anhydride

→

87

Ausbeute 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

Ausbeute 91.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle