تفاعل #1755468

معادلة التفاعل

86

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

pyridine

acetic anhydride

→

87

المردود 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

المردود 91.4%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 16 hours
2. 2
   درجة الحرارةThe reaction mixture was heated at 75° C. for 3 hours
3. 3
   أخرىThe solvent was removed under reduced pressure
4. 4
   أخرىto yield a yellow oil which
5. 5
   أخرىwas purified by flash chromatography, on silica gel
6. 6
   غسيلeluting with 1:3 ether/petroleum ether

الإجراء التجريبي

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).

المصدر