HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl formate → methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl formate | HCID 7865 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate | HCID 21936211 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | methyl(2Z)-3-hydroxy-2-{[2-(trifluoromethyl)-5-pyrimidinyl]methyl}-2-propenoate | HCID 67953508 | 82% |
Reaction Steps
To a solution of NaH (360 mg, 9.00 mmol) in DME (20 mL) was added a solution of methyl formate (0.254 mL, 4.10 mmol) and methyl 3-[2-(trifluoromethyl)-5-pyrimidinyl]propanoate (800 mg, 3.42 mmol) in DME (20 mL) at 0° C. The mixture was stirred at room temperature overnight, and quenched with MeOH. Purification via reverse phase flash chromatography afforded the title compound (730 mg, 2.78 mmol, 82% yield) as yellow solid. LCMS: rt=2.03 min, [M+H+]=263.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-f1ff2c5bd4a04857acab803daf319a93 |
| Source note | uspto-grants-2014_01 |