Water → ethyl (E)-3-(3-quinolinyl)acrylate

HRID 2229240Notes

Reaction equation

HRID 2229240 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=O)[CH:2]=1.C(OP([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(OCC)=O)C.[H-].[Na+].O>C1COCC1.C(OCC)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](/[CH:11]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 836413-Quinolinecarboxaldehyde

Product 1

HCID 12478192ethyl (E)-3-(3-quinolinyl)acrylateYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Quinolinecarbaldehyde (5.03 g) was added to a mixture of ethyl diethylphosphonoacetate (9.31 g) and NaH (60% oil dispersion,0.791 g) in THF under ice cooling. The mixture was stirred at room temperature for 14 hours. To the mixture were added water and ethyl acetate. The organic layer was washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane-ethyl acetate=10:1) followed by crystallization from CH2Cl2-cyclohexane to give the titled compound (3.20 g) as a colorless solid.

Workup

  1. washThe organic layer was washed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (hexane-ethyl acetate=10:1)
  5. customfollowed by crystallization from CH2Cl2-cyclohexane

Sources & evidence

ORD record
ord-a428caebdffa44269946d9d4b8407adb
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

Loading…