Pyridine → 12-(Acryloyloxy)dodecanoic acid

HRID 1734970ノート

反応式

HRID 1734970 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.[C:22](Cl)(=[O:25])[CH:23]=[CH2:24]>O1CCCC1>[C:22]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])(=[O:25])[CH:23]=[CH2:24]

参加物

5

反応物 3

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 7903412-Hydroxydodecanoic Acid

生成物 1

HCID 2232822312-(Acryloyloxy)dodecanoic acid収率 40.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

12-Hydroxydodecanoic acid (5.0 g, 0.023 mol) dissolved in tetrahydrofuran (100 ml) and pyridine (2.16 g, 0,027 mol) was cooled to 0° C. Acryloyl chloride (3.15 g, 0.023 mol) in tetrahydrofuran (75 ml) was then added dropwise to the solution. The mixture was stirred for 5 hours at 0° C. then stirred overnight at room temperature. The precipitated pyridinium salt was filtered off and the solvent removed under vacuum. The resulting liquid was purified by flash chromatography (silica gel/chloroform) to give 2.5 g (40%) of the title compound. 1H NMR (60 MHz, CDCl3): δ1.20 (s, 18H, CH2), 2.15 (m, 2H, CH2COOH), 4.0 (m, 2H, COOCH2), 5.7-6.0 (m, 3H, CH2 =and =CH).

後処理

  1. stirringthen stirred overnight at room temperature
  2. filtrationThe precipitated pyridinium salt was filtered off
  3. customthe solvent removed under vacuum
  4. customThe resulting liquid was purified by flash chromatography (silica gel/chloroform)

出典と根拠

ORDレコード
ord-bff71cdb8d7a4b18bc2f3eec85f2dc55
出典データセット
uspto-grants-1996_07
特許番号
US05536490

反応ノート

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