Acetic Acid → Ethyl 3-methylpent-4-enoate

反応式

[CH2:1](O)/[CH:2]=[CH:3]/[CH3:4].C(O[C:9]([O:14]CC)([O:11][CH2:12][CH3:13])[CH3:10])C.C(O)(=O)C>>[CH3:4][CH:3]([CH:2]=[CH2:1])[CH2:10][C:9]([O:11][CH2:12][CH3:13])=[O:14]

参加物

反応物 3

HCID 176Acetic Acid

HCID 66221Triethyl orthoacetate

HCID 637922trans-Crotyl alcohol

生成物 1

HCID 12476290Ethyl 3-methylpent-4-enoate収率 71%

反応条件

温度: 125 °C

実験手順

To a solution of (E)-but-2-en-1-ol (50 g, 693 mmol) in 1,1,1-triethoxyethane (890 mL 4854 mmol) was added acetic acid (5 g, 83 mmol) at room temperature. The reaction was heated to 125° C. for 4 h. The by-product ethanol was distilled by normal distillation to get crude compound ethyl 3-methylpent-4-enoate (70 g, 71.0%) as color less oil. This was taken to next step without further purification; 1H NMR (DMSO-d6) δ ppm 5.82-5.73 (m, 1H), 5.03-4.92 (m, 2H), 4.08-4.02 (m, 2H), 2.50 (m, 1H), 2.31-2.26 (m, 2H), 1.17 (t, J=8 Hz, 3H), 1.00 (d, J=8 Hz, 3H).