Reaction #1755468

Reaction equation

86

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

pyridine

acetic anhydride

→

87

Yield 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

Yield 91.4%

Solvents

DMF

Conditions

Workup

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

Procedure

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