Water → Ethyl 2,3-methylenedioxycinnamate

HRID 59608

반응식

HRID 59608 반응식
[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

참가 물질

5

반응물 4

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 822641,3-Benzodioxole-4-carboxaldehyde

생성물 1

HCID 68513084Ethyl 2,3-methylenedioxycinnamate수율 92%

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ae57d704f83844aeb66afa1dddeec2d9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440926B2

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