Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 68780462 | HCID 68780462 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68779597 | HCID 68779597 | 42.1% |
Reaction Steps
1.10 g 4-Methoxymethyl-2-[2-(4-methoxy-phenyl)-vinyl]-oxazole-5-carboxylic acid methyl ester were dissolved in 15 ml tetrahydrofuran and added to a ice cooled solution of 137 mg lithium aluminium hydride in 7 ml tetrahydrofuran. The reaction mixture was stirred at 0° C. for one hour. Then 50 ml ethyl acetate and 20 ml saturated NH4Cl solution were added. The precipitate was filtered off through a celite pad and washed with ethyl acetate. The organic layer of the filtrate was separated. The aqueous layer of the filtrate was extracted two times with portions of 100 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the residue purified by RP-HPLC to obtain to 420 mg {4-methoxymethyl-2-[2-(4-methoxy-phenyl)-vinyl]-oxazol-5-yl}-methanol as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07851493B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-83eace48dbc2472a911a4eb3a6f48f3e |
|---|
| Source note | uspto-grants-2010_12 |
|---|