Ethanol → HCID 22131260, compound

HRID 1857569Notes

Reaction equation

HRID 1857569 reaction equation
[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][CH2:5][C:6](OC)([CH:19]=2)[CH:7]=[C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:2]1.[BH4-].[Na+].[CH2:26]([OH:28])C>>[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][C:5]([O:28][CH3:26])=[C:6]([CH:19]=2)[CH2:7][CH:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:2]1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 22993835HCID 22993835, compound

Product 1

HCID 22131260HCID 22131260, compoundYield 86%

Procedure

To a solution of the diethyl 2-(4,5-methylenedioxy-1-methoxybenylidene)-malonate (23.40 g, 0.073 mol) in ethanol (100 mL) was added sodium borohydride (2.80 g, 0.073 mol) and the mixture was stirred at room temperature for 5 h. The reaction was quenched with water and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (Na2SO4) and evaporated to afford the title compound as an oil (20.30 g, 86%): 1H NMR (250 MHz, CDCl3) δ 7.45 (d, J=10 Hz, 1H), 7.20 (d, J=15 Hz, 1H), 5.85 (s, 2H), 4.22 (m, 4H), 3.40 (s, 2H), 3.30 (s, 3H), 1.25 (m, 6H).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-db947da1ef344a0f8f734dc916badeb2
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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