Trimethylsilyldiazomethane → Methyl 3-cyano-4-isopropoxybenzoate

To 3-cyano-4-isopropoxybenzoic acid (0.3 g, 1.462 mmol) in a mixture of dichloromethane (4 mL) and MeOH (1.00 mL) was added trimethylsilyldiazomethane (0.950 mL, 1.9 mmol) dropwise over a period of 3 min at 0° C. The pale yellow solution was allowed to come to room temperature over a period of 15 min. and stirred at room temperature for 1.5 h. Excess trimethylsilyldiazomethane was quenched by the slow addition of acetic acid (˜0.5 ml) at room temperature until the yellow color was discharged. The reaction mixture was concentrated and partitioned between ether (20 mL) and sat. aq. sodium bicarbonate (10 mL). The ether layer was washed with brine (10 mL), dried over sodium sulfate and concentrated. The resulting oil was azeotroped with THF (5 mL) and dried under high vacuum to yield methyl 3-cyano-4-isopropoxybenzoate (0.32 g, 1.460 mmol, 100% yield) as an oil. LC/MS M+1=219.9.

1. customExcess trimethylsilyldiazomethane was quenched by the slow addition of acetic acid (˜0.5 ml) at room temperature until the yellow color
2. concentrationThe reaction mixture was concentrated
3. custompartitioned between ether (20 mL) and sat. aq. sodium bicarbonate (10 mL)
4. washThe ether layer was washed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe resulting oil was azeotroped with THF (5 mL)
8. customdried under high vacuum

ORD record

ord-6c616f9ba4d14a7a97b072a05bf43a46

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2