Ethanol → HCID 11728274, compound

HRID 233288Notes

Reaction equation

HRID 233288 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([C:29]#[N:30])C(OCC)=O)=[CH:18][CH:17]=2)[N:12]=1.[OH-].[Na+].C(O)C.O>ClC1C=CC=CC=1Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH3:31])=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:29]#[N:30])=[CH:20][CH:21]=2)[N:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 23361366HCID 23361366, compound

Product 1

HCID 11728274HCID 11728274, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of ethyl 3-[4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]phenyl]-2-cyanopropionate (2.24 g), 1N NaOH (15 ml) and ethanol (50 ml) was stirred for one hour at room temperature. The reaction mixture was poured into water and made acidic, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure to leave a crystalline product, which was added to pyridine (5 ml)--o-dichlorobenzene (50 ml), and the mixture was heated for 2 hours under reflux. The reaction mixture was concentrated under reduced pressure, which was subjected to a silica gel column chromatography. From the fractions eluted with chloroform was obtained 3-[4-[2-[2-(2-chlorophenyl)-5-methyl-4-oxazolyl]ethoxy]phenyl]propionitrile (1.5 g, 80%), which was recrystallized from dichloromethane--isopropyl ether to give pale yellow crystals, m.p.88°-89° C.

Workup

  1. extractionwhich was subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto leave a crystalline product, which
  6. temperatureunder reflux
  7. concentrationThe reaction mixture was concentrated under reduced pressure, which
  8. washFrom the fractions eluted with chloroform

Sources & evidence

ORD record
ord-080430fe1dd24dd3a3387cf0ce6c6634
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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