Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 10535422 | HCID 10535422 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 59739573 | HCID 59739573 | 123.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680290B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-84e7d8ce7f24449f9d76e83aa2cdd066 |
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| Source note | uspto-grants-2014_03 |
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