反応 #1755468

反応方程式

86

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

pyridine

acetic anhydride

→

87

収率 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

収率 91.4%

溶媒

DMF

反応条件

後処理

1. 1
   workup.WAITAfter 16 hours
2. 2
   温度The reaction mixture was heated at 75° C. for 3 hours
3. 3
   その他The solvent was removed under reduced pressure
4. 4
   その他to yield a yellow oil which
5. 5
   その他was purified by flash chromatography, on silica gel
6. 6
   洗浄eluting with 1:3 ether/petroleum ether

実験手順

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).

出典