Water → Ethyl 2,3-methylenedioxycinnamate

HRID 59608

Reaction equation

HRID 59608 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 68513084Ethyl 2,3-methylenedioxycinnamateYield 92%

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ae57d704f83844aeb66afa1dddeec2d9
Source dataset
uspto-grants-2016_09
Patent number
US09440926B2

Linked notes

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