HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol | HCID 10559114 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropyl acetate | HCID 66669740 | 60.7% |
Reaction Steps
To a solution of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol (172 mg, 1 mmol) and acetic acid (120 mg, 2 mmol, Shantou Xilong chemical factory) in 2 mL of DCM was added DMAP (12 mg, 0.1 mmol, aladdin) at rt. After stirring for 30 min, DCC (840 mg, 4 mmol, Aldrich) was added at 0° C. The reaction was quenched with water after all of 1-((tetrahydro-2H-pyran-2-yloxy)methyl)cyclopropanol disappeared (monitored by TLC) (about 4 hours). The solid formed during the reaction was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE: EtOAc=20:1) to give the desired compound as yellow oil (130 mg, 60.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08232294B2 |
| Source dataset | uspto-grants-2012_07 |
| ORD ID | ord-c2466afe4fd5427fa9e0aaba28c1b0af |
| Source note | uspto-grants-2012_07 |