ChemicalBook CAS DataBase List 2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile

2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile synthesis

9synthesis methods

Product Name:2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile
CAS Number:96042-30-7
Molecular formula:C19H17N3O
Molecular Weight:303.36

2905-54-6 Synthesis

2905-54-6
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$9.00/1g

38594-42-2 Synthesis

38594-42-2
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$12.00/250mg

2-[2-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile

96042-30-7
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Yield:38594-42-2 88%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran;ethyl acetate;

Steps:

35.b b)

b)
(2,3-dichlorophenyl)methanol
A suspension of LiAlH₄ (7.4 g, 0.195 mol) in THF (500 mL) was stirred at 0° C. A solution of methyl 2,3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 mL) was added dropwise into the above mixture at 0-5° C.
Then the mixture was stirred at room temperature for 2 h.
The reaction mixture was quenched with ethyl acetate (15 mL), water (7.5 mL), 15% NaOH (7.5 mL) and water (22.5 mL), filtered and the filtrate was concentrated.
The resulting residue was dissolved with DCM (500 mL) and washed with brine.
The organic layer was dried over Na₂SO₄, filtered and the filtrate was concentrated to provide the titled compound (37 g, 88%), as a white solid; ¹H NMR (300 MHz, CDCl₃) δ ppm 4.81 (d, J=6.3 Hz, 2H), 7.24 (t, J=7.8 Hz, 1H), 7.42-7.45 (m, 2H).

References:

US9096605,2015,B2