HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 23023492, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Methyl tetrahydrofuran-2-carboxylate | HCID 169922 | — |
| Reactant | 3-Methoxybenzyl bromide | HCID 4067207 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23023492 | HCID 23023492 | 59% |
Reaction Steps
To a solution of 4.44 g of diisopropylamine in 20 ml of tetrahydrofuran were sequentially added 26 ml of 1.6 M solution of n-butyllithium in hexane, 5.30 g of methyl tetrahydro-2-furancarboxylate in 20 ml of tetrahydrofuran and 8.85 g of 1-bromomethyl-3-methoxybenzene in 25 ml of tetrahydrofuran at −70° C. under an atmosphere of nitrogen gas. After warming to room temperature, 100 ml of 1N hydrochloric acid and 200 ml of ethyl acetate were added. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 6.01 g of the title compound from the 4:1 hexane-ethyl acetate fraction.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07371777B2 |
| Source dataset | uspto-grants-2008_05 |
| ORD ID | ord-3ea028b35f894ef99fe94cacefb314ca |
| Source note | uspto-grants-2008_05 |