Methanol → HCID 59739573, compound

Temperature

40 °C

5-Cyano-4-methoxycarbonyl-3-methyl-isothiazole (1.14 g, 6.3 mmol) was dissolved in diethyl ether (20 ml) and methanol (0.38 ml, 9.4 mmol). Lithium borohydride (204 mg, 9.4 mmol) was added and the mixture was stirred at 40° C. for 2 hours. The reaction was quenched by addition of aqueous hydrochloric acid (1M) (20 ml). The two phases were separated and the aqueous phase was extracted with diethyl ether (2×20 ml). The combined organic phases were dried over magnesium sulfate and concentrated to give a crude product (1.2 g), which consisted of a 1:1 mixture of methyl ester and product. The mixture was used without further purification.

1. customThe reaction was quenched by addition of aqueous hydrochloric acid (1M) (20 ml)
2. customThe two phases were separated
3. extractionthe aqueous phase was extracted with diethyl ether (2×20 ml)
4. dry with materialThe combined organic phases were dried over magnesium sulfate
5. concentrationconcentrated

ORD record

ord-84e7d8ce7f24449f9d76e83aa2cdd066

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680290B2