4-(1,3-Dioxolan-2-yl)benzonitrile → HCID 22502706, compound

Temperature

-70 °C

To a solution of N-methyl-2-methylthiophene-3-carboxamide (18.5 g) in tetrahydrofuran (350 ml) was dropwise added 2.5M n-butyl lithium (100 ml) at −70° C. The resulting solution was stirred at −70° C. for 1.5 hr, followed by the addition of a solution of 4-(1,3-dioxolan-2-yl)benzonitrile (20.9 g) in tetrahydrofuran (100 ml) at once. After the dry ice/acetone bath was removed, the reaction mixture was back to room temperature. Three hours later, an aqueous solution of saturated ammonium chloride was added thereto, and the organic layer was separated, washed with water and dried. The filtrate was concentrated, and the resulting solid was washed with ethyl acetate, tetrahydrofuran/ether and n-hexane in this order. The resulting solid was then dried, to give the title compound as white crystals (6.24 g, yield; 31.7%).

1. customat −70° C
2. customAfter the dry ice/acetone bath was removed
3. customwas back to room temperature
4. additionThree hours later, an aqueous solution of saturated ammonium chloride was added
5. customthe organic layer was separated
6. washwashed with water
7. customdried
8. concentrationThe filtrate was concentrated
9. washthe resulting solid was washed with ethyl acetate, tetrahydrofuran/ether and n-hexane in this order
10. customThe resulting solid was then dried

ORD record

ord-e64e9493b72c47bb9f9ff8718e0cec0e

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06340759B1