Hydrochloric Acid → HCID 86591380, compound

HRID 1794390Notes

Reaction equation

HRID 1794390 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH:12]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OP([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(OCC)=O)C.[H-].[Na+].Cl>CN(C)C=O>[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2/[CH:12]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 22221089HCID 22221089, compound

Product 1

HCID 86591380HCID 86591380, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-phenylisoxazole-4-carbaldehyde (7.18 g), ethyl diethylphosphonoacetate (9.35 g) and N,N-dimethylformamide (150 ml) was added sodium hydride (60%, oil, 1.65 g) at 0° C., and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl (E)-3-(5-phenyl-4-isoxazolyl)propenoate (8.88 g, yield 88%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). NMR (CDCl3) δ: 1.33 (3H, t, J=7.2 Hz), 4.27 (2H, q, J=7.2 Hz), 6.34 (1H, d, J=15.4 Hz), 7.48–7.82 (6H, m), 8.52 (1H, s).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c000f0856f8b49118fbca688cd5a3a00
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…