Pyridine → 9-Dodecenyl acetate, (9Z)-

HRID 879037ノート

反応式

HRID 879037 の反応式
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\CC>C(Cl)Cl.C(OCC)C>[C:5]([O:4][CH2:1][CH2:2][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]\[CH2:15][CH3:14])(=[O:7])[CH3:6]

参加物

6

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 64313429-Dodecen-1-ol, (9Z)-

生成物 1

HCID 53634059-Dodecenyl acetate, (9Z)-収率 87%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Acetic anhydride (0.17 mL, 1.8 mmol), then pyridine (90 μL, 1.1 mmol), were added sequentially to alcohol 7 (0.17 g, 0.93 mmol) in CH2Cl2 (1.8 mL), and stirred at room temperature for 17 hours. The mixture was diluted with diethyl ether, washed with saturated aqueous NaHCO3, then brine, dried with Na2SO4, and concentrated. Flash chromatography of the residue (SiO2, 5% EtOAc in hexanes) provided 8 (0.18 g, 87% yield, 74% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.28-5.43 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.04 (7H, m), 1.61 (2H, td, J=9.8, 8.7, 4.6 Hz), 1.29 (10H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 171.3, 131.6, 129.3, 64.7, 32.6, 29.8, 29.5, 29.3, 29.2, 28.7, 26.0, 21.1, 20.6, 14.5; HRMS (FAB): 227.2045, [C14H26O2+H]+ requires 227.2006.

後処理

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialbrine, dried with Na2SO4
  3. concentrationconcentrated
  4. customFlash chromatography of the residue (SiO2, 5% EtOAc in hexanes) provided 8 (0.18 g, 87% yield, 74% Z as determined by 13C-NMR) as a colorless oil

出典と根拠

ORDレコード
ord-b686bf678fb84fc7ae1ce9cfe59676f2
出典データセット
uspto-grants-2015_03
特許番号
US08987531B2

反応ノート

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