HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 3-formylbenzoate → 2-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 3-formylbenzoate | HCID 639145 | — |
| Reactant | 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl)-pyridine | HCID 15661708 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | 2-[(1RS)-1-Hydroxy-1-(3-methoxycarbonylphenyl)-methyl]-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine | HCID 15661716 | 25.5% |
Reaction Steps
Under the conditions of example 1B, 326 mg of 2-bromo-6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-pyridine is reacted with 1.38 ml of n-butyllithium (1.6 molar in hexane) and 181 mg of 3-formylbenzoic acid methyl ester (J. Org. Chem. 31, 1966, 2585), worked up and chromatographed on silica gel with hexane/ethyl acetate 8/2. 105 mg of the title compound is obtained as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614634 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-a8063f5cd9c8453c96cd94b232c273f7 |
| Source note | uspto-grants-1997_03 |