反应 #1755444

反应方程式

Furfuryl alcohol

triethylamine

isobutyryl chloride

→

Furfuryl Isobutyrate

收率 87.5%

溶剂

THF

dichloromethane

反应条件

后处理

1. 1
   过滤filtered through a celite plug
2. 2
   其他to remove the triethylammonium chloride
3. 3
   其他the solvent was removed under vacuum
4. 4
   其他The residue was purified by silica column chromatography
5. 5
   其他to give an oil (8.5 g 87.5% yield)

实验过程

Furfuryl alcohol (5 mL, 1 eq.) was dissolved in THF (20 mL) in a dry, round bottomed flask and stirred with triethylamine (10 mL, 1.25 eq.). The solution was cooled to 5° C. and isobutyryl chloride (60.1 mL, 1.0 eq.) was added dropwise. The mixture was stirred for 2 h at 20° C. The reaction was worked up by diluting with dichloromethane (30 mL) and filtered through a celite plug to remove the triethylammonium chloride, and the solvent was removed under vacuum. The residue was purified by silica column chromatography using tert-butylmethyl ether-hexane (1:5) (Rf 0.54) to give an oil (8.5 g 87.5% yield). IR (cm−1): 1737 (C═O st), 3145, 3124 (═C—H st), 816, 745 (C—H δ, furan ring). 1H NMR (CDCl3, 300 MHz): δ 2.57 (sept, 1H, C—H(CH3)2, J=6.9 Hz), 1.17 (d, 6H, CH(CH3)2, J=6.9 Hz), 5.06 (s, 2H, CH2O) ppm. Furan ring: 6.39 (bd, 1H, H-3′, J3′,4′=3.3 Hz), 6.35 (dd, 1H, H-4′, J4′,5′=1.8 Hz), 7.41 (m, 1H, H-5′) ppm. 13C NMR (CDCl3, 75 MHz): δ 176.7 (C═O), 33.9 [CH(CH3)2], 18.9 [CH(CH3)2] ppm. Furan ring: 149.8 (C-2′), 110.5, 110.3 (C-3′, C-4′), 143.1 (C-5′) ppm. CI-Mass Spectrometry. m/z: 168 (M+), 97 [(OCH2-fur)+], 81 (main peak) [(CH2-fur)+], 71 [(CH3)2CHCO)+]. HRMS: Theoretical molecular weight for C9H12O3 (M+) 168.078644, experimental molecular weight: 168.078182.

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