1-NAPHTHOYLACETONITRILE synthesis

5synthesis methods

Product Name:1-NAPHTHOYLACETONITRILE
CAS Number:39528-57-9
Molecular formula:C13H9NO
Molecular Weight:195.22

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75-05-8 Synthesis

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Yield:39528-57-9 72%

Reaction Conditions:

Stage #1: acetonitrilewith n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;
Stage #2: ethyl 1-naphthoate in tetrahydrofuran;hexane at -78 - 20; for 2 h;

Steps:

B.2b-B.1 Step 1:
1-Naphthoylacetonitrile

Step 1:
1-Naphthoylacetonitrile
To a solution of 2.50 M of n-butyllithium in hexane (49.9 mL, 125 mmol) in tetrahydrofuran (49.9 mL) cooled to -78° C. is added acetonitrile (6.52 mL, 125 mmol) drop-wise.
The resulting cloudy mixture is stirred for 30 min.
Ethyl α-napthoate (8.87 mL, 49.9 mmol) is added drop-wise and the reaction mixture is stirred at -78° C. for 2 hr.
The reaction is warmed to room temperature, quenched with acetic acid (50 ml) and partitioned between ethyl acetate and water.
The organic layer is dried over Na₂SO₄, filtered and concentrated in vacuo.
The crude material is purified by column chromatography (eluent: 5-15% CH₂Cl₂/methanol) to provide 1-naphthoylacetonitrile (6.99 g, yield 72%).
¹H NMR (400 MHz, CDCl₃) δ 8.82 (d, J=8.7 Hz, 1H), 8.11 (d, J=8.3 Hz, 1H), 7.90 (t, J=8.1 Hz, 2H), 7.71-7.64 (m, 1H), 7.57 (dt, J=15.5, 7.2 Hz, 2H), 4.21 (s, 2H).