Diethyl Ether → 3-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanal

HRID 1838273Notes

Reaction equation

HRID 1838273 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]2[CH2:26][CH:25]([CH2:27][CH2:28][CH2:29][OH:30])[O:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21].C(OCC)C>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([C:22]2[CH2:26][CH:25]([CH2:27][CH2:28][CH:29]=[O:30])[O:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18753376HCID 18753376, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 187533883-[3-(3,4-Dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propanalYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After dissolving pyridinium chlorochromate (PCC; 2.249 g, 10.435 mmol) and 70-230 mesh SiO2 (2.748 g) in 25 mL of methylene chloride, 3-[3-(3,4-dimethoxyphenyl)-4,5-dihydroisoxazol-5-yl]propan-1-ol (1.374 g, 5.217 mmol) dissolved in 2 mL of methylene chloride was added. After the reaction was continued for about 6 hr, 10 mL of diethyl ether was added and the reaction mixture was filtered through a cellite bed. After removing all the solvent and purifying by column chromatography on silica gel (hexane/ethyl acetate=1.5/1, v/v), 0.72 g (51.6%) of the target compound was obtained.

Workup

  1. additionwas added
  2. filtrationthe reaction mixture was filtered through a cellite bed
  3. customAfter removing all the solvent
  4. custompurifying by column chromatography on silica gel (hexane/ethyl acetate=1.5/1

Sources & evidence

ORD record
ord-d9c44c5ed7824149b52e83fdb5948cad
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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