Water → Ethyl 2,3-methylenedioxycinnamate

HRID 59608

反応式

HRID 59608 の反応式
[H-].[Na+].[CH2:3]1[O:13][C:12]2[C:5](=[C:6]([CH:9]=[CH:10][CH:11]=2)[CH:7]=O)[O:4]1.[OH2:14].[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[CH2:3]1[O:13][C:12]2[C:5](=[C:6]([CH:9]=[CH:10][CH:11]=2)[CH:7]=[CH:17][C:16]([O:15][CH2:19][CH3:18])=[O:14])[O:4]1

参加物

5

反応物 4

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 822641,3-Benzodioxole-4-carboxaldehyde

生成物 1

HCID 68513084Ethyl 2,3-methylenedioxycinnamate収率 92%

反応条件

温度
0 °C

実験手順

Triethyl phosphonoacetate (4.05 mL, 20.2 mmol) was added dropwise to a stirred suspension of sodium hydride (0.80 g, 20 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 20 minutes. A solution of 2,3-methylenedioxybenzaldehyde (2.50 g, 16 mmol) in tetrahydrofuran (10 mL) was added dropwise at 0° C. The mixture was stirred for 2 hours during which time it was allowed to warm to room temperature. The mixture was poured into water (250 mL), and extracted with ethyl acetate (3×250 mL). The combined organic extracts were then washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed over silica gel. Elution with ethyl acetate/hexanes (1:10) gave ethyl 2,3-methylenedioxycinnamate as a colourless solid (3.50 g, 92%).

後処理

  1. stirringThe mixture was stirred for 2 hours during which time it
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate (3×250 mL)
  4. washThe combined organic extracts were then washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed over silica gel
  8. washElution with ethyl acetate/hexanes (1:10)

出典と根拠

ORDレコード
ord-ae57d704f83844aeb66afa1dddeec2d9
出典データセット
uspto-grants-2016_09
特許番号
US09440926B2

関連ノート

読み込み中…