반응 #1755468

반응 방정식

86

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

pyridine

acetic anhydride

→

87

수율 91.4%

(4-prop-2-ynylcyclohexyl)methyl acetate

수율 91.4%

용매

DMF

반응 조건

후처리

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

실험 절차

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).

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