Water → HCID 53895771, compound

HRID 1906030Notes

Reaction equation

HRID 1906030 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19].CN1CCOCC1.O>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl.C(OCC)C>[O:19]=[C:18]([CH:20]=[CH:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)[CH2:17][C:16]([O:22][CH2:23][CH3:24])=[O:21]

Participants

9

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 8868Ethyl AcetoacetateHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 53895771HCID 53895771, compound

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 0.10 moles of titanium tetrachloride in 25 ml of carbon tetrachloride was added with rapid stirring over 15 minutes to 200 ml of cold (0°) tetrahydrofuran. After the mixture was stirred an additional 15 minutes, a solution of 0.05 moles of 3-phenoxybenzaldehyde in 15 ml of tetrahydrofuran was added over 30 minutes. A solution of 0.05 moles of ethyl acetoacetate in 15 ml of tetrahydrofuran was then added. A solution of 22 ml of N-methylmorpholine in 30 ml of tetrahydrofuran was added dropwise over three hours. The reaction mixture was then stirred for 20 hours, after which time 50 ml of water and 50 ml of diethyl ether were added. After the resultant layers were separated, the aqueous layer was extracted with 50 ml of diethyl ether. The diethyl ether extract was combined with the initially separated organic layer, dried over sodium sulfate, filtered, and concentrated in vacuo to an oil. Chromatography on silica gel gave the title compound as an oil. Structure assignment was supported by nmr and infrared spectra and by elemental analysis.

Workup

  1. stirringThe reaction mixture was then stirred for 20 hours
  2. customAfter the resultant layers were separated
  3. extractionthe aqueous layer was extracted with 50 ml of diethyl ether
  4. extractionThe diethyl ether extract
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-2ce59c0fe20f471b82f32be8715846e0
Source dataset
uspto-grants-1987_03
Patent number
US04649157

Reaction notes

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