Triethylamine → 2-(4-Methylphenoxy)-2-(2'-chlorophenyl)acetonitrile
Reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]([NH2:10])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]#[N:10])=[CH:18][CH:19]=1Participants
4
Procedure
The product of Step A (0.650 g, 2.36 mmol) was added to phosphorous oxychloride (5.95 mL, 27 eq) at 0° C. followed by slow addition of 0.73 mL (2.2 eq) of triethylamine. The reaction mixture was warmed to room temperature for 10 minutes, refluxed for 50 minutes and then cooled to room temperature. The reaction mixture was concentrated in vacuo, and partitioned between ice water and toluene. The aqueous layer was extracted 3 times with toluene, and the combined toluene extracts were washed with 0.5N NaOH and H2O. The crude product was concentrated in vacuo and purified on a silica gel flash chromatography column (140×30 mm) eluted with 2% ethyl acetate/hexane to afford 0.555 g (91%) of the title compound.
Workup
- temperaturerefluxed for 50 minutes
- temperaturecooled to room temperature
- concentrationThe reaction mixture was concentrated in vacuo
- custompartitioned between ice water and toluene
- extractionThe aqueous layer was extracted 3 times with toluene
- washthe combined toluene extracts were washed with 0.5N NaOH and H2O
- concentrationThe crude product was concentrated in vacuo
- custompurified on a silica gel flash chromatography column (140×30 mm)
- washeluted with 2% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-655e8f1ff020465a9a02976c606c2b56
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05240938
Reaction notes
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