HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one → (S)-4-Benzyl-3-[(R)-2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one | HCID 15597770 | — |
| Reactant | 2-Bromomethyl-1,3-dichloro-5-benzyloxy-benzene | HCID 59299428 | — |
| Reactant | HCID 178418261 | HCID 178418261 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (S)-4-Benzyl-3-[(R)-2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one | HCID 66905125 | — |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
Dissolve 4-Benzyl-3-pent-4-enoyl-oxazolidin-2-one (2.21 g, 8.52 mmol) in 25 ml of dry THF. Chilled to −78° C. Add LiN(TMS)2 (10.23 ml, 10.23 mmol). Stir for 30 min at same temperature. Add 5-Benzyloxy-2-bromomethyl-1,3-dichloro-benzene (3.10 g, 8.95 mmol) in 5 ml of THF. Let the reaction slowly warm to room temperature.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153807B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-b95a392fc67a46618b6465454907f492 |
| Source note | uspto-grants-2012_04 |