Water → Ethyl 2,3-methylenedioxycinnamate

HRID 1184671Notes

Reaction equation

HRID 1184671 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, 202 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, 16.7 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-94d263307dc946c2a1c1579f0dcc760a
Source dataset
uspto-grants-2014_03
Patent number
US08669280B2

Reaction notes

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