Pyridine → 11-Tetradecenyl acetate, (11Z)-

HRID 879039

反応式

HRID 879039 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]\[CH2:24][CH3:25].CCOC(C)=O>C(Cl)Cl.C(OCC)C>[C:5]([O:4][CH2:1][CH2:2][CH2:25][CH2:24][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

7

反応物 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 64313429-Dodecen-1-ol, (9Z)-

生成物 1

HCID 536769211-Tetradecenyl acetate, (11Z)-収率 84%

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 (86 μL, 1.1 mmol), were added sequentially to alcohol 7 (0.19 g, 0.89 mmol) in CH2Cl2 (1.8 mL), and stirred at room temperature for 12 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 10 (0.19 g, 84% yield, 77% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.43 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.04 (7H, m), 1.61 (2H, m), 1.27 (14H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 171.4, 131.7, 129.4, 64.8, 32.7, 29.9, 29.7 (2C), 29.4 (2C), 28.7, 27.2, 26.1, 21.2, 20.7, 14.6; HRMS (FAB): 255.2324, [C16H30O2+H]+ requires 255.2319.

後処理

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialbrine, dried with Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-9fe16c1ab2ad4d1094adb4f38fd21263
出典データセット
uspto-grants-2015_03
特許番号
US08987531B2

関連ノート

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