Ethanol → HCID 23293688, compound

HRID 2289162Notes

Reaction equation

HRID 2289162 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:14]([O:16][C:17](=[O:27])[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[CH3:15].CCO>C1COCC1>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:19]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:27])[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 367202Ethyl 3-(3-fluorophenyl)-2-propenoate

Product 1

HCID 23293688HCID 23293688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (1.59 g, 63.1 mmol) in 200 mL THF was added diethyl malonate (10.0 g, 62.4 mmol) gradually. The reaction mixture was stirred for 1 hr at room temperature. 3-(3-Fluorophenyl)acrylic acid ethyl ester (2-1) (11.1 g, 57.2 mmol; prepared via standard procedures from 3-fluorocinnamic acid) and EtOH (5 mL) are added. The mixture was then stirred at 90° C. for 12 hr, concentrated under diminished pressure and treated with 50 mL 10% sodium hydrogencarbonate solution. The aqueous mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried (Na2SO4). After solvent removal, the residue was purified using silica gel flash chromatography (6:1 hexane/EtOAc) to give 2-2 as an oil.

Workup

  1. stirringThe mixture was then stirred at 90° C. for 12 hr
  2. concentrationconcentrated under diminished pressure
  3. additiontreated with 50 mL 10% sodium hydrogencarbonate solution
  4. extractionThe aqueous mixture was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customAfter solvent removal
  8. customthe residue was purified

Sources & evidence

ORD record
ord-25579edb96694398a3bf540f185cf94b
Source dataset
uspto-grants-2000_07
Patent number
US06090944

Reaction notes

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