Diethyl Ether → HCID 54356193, compound

HRID 2413352Notes

Reaction equation

HRID 2413352 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:33]=[CH:32][C:29](C=O)=[CH:28][CH:27]=2)=[CH:21][N:20]=1.[CH2:34](OCC)[CH3:35].O1CCC[CH2:40]1>O>[CH2:34]([C:8](=[CH:9][C:29]1[CH:28]=[CH:27][C:26]([O:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH3:40])=[N:20][CH:21]=2)=[CH:33][CH:32]=1)[C:6]([O:5][CH2:4][CH3:3])=[O:7])[CH3:35]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionateHCID 13392574HCID 13392574, compound

Product 1

HCID 54356193HCID 54356193, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 g of sodium hydride (50%) was added to 50 ml of tetrahydrofuran and 10 g of triethyl 2-phosphonopropionate was added dropwise to the mixture. A solution of 7.0 g of 4-(2-methyl-5-pyridyloxy)benzaldehyde in 20 ml of tetrahydrofuran was added dropwise to the mixture, followed by stirring for 3 hours. Diethyl ether and water were added to the reaction mixture and the organic layer was separated, washed with water and extracted with 10% hydrochloric acid. The aqueous layer was washed with diethyl ether, rendered alkaline with sodium carbonate and extracted with diethyl ether. The ether layer was washed with water and dried over magnesium sulfate. The solvent was distilled off and the resulting oily substance was purified by silica gel chromatography (eluted with dichloromethane-hexane, 1:1 to 2:1 by volume) to obtain 6.0 g (61% yield) of ethyl 2-ethyl-3-[4-(2-ethyl-5-pyridyloxy)phenyl]propenoate as a colorless oil having a boiling point of 170° C./2 mmHg (bath temperature).

Workup

  1. additionwas added dropwise to the mixture
  2. customthe organic layer was separated
  3. washwashed with water
  4. extractionextracted with 10% hydrochloric acid
  5. washThe aqueous layer was washed with diethyl ether
  6. extractionextracted with diethyl ether
  7. washThe ether layer was washed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe resulting oily substance was purified by silica gel chromatography (eluted with dichloromethane-hexane, 1:1 to 2:1 by volume)

Sources & evidence

ORD record
ord-f76f7462d361478db57c48d49120cd93
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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