HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,4-dihydro-2H-pyran → HCID 15482800, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | (S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone | HCID 2733813 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15482800 | HCID 15482800 | 88.1% |
Reaction Steps
To a mixture of (S)-5-(hydroxymethyl)-dihydrofuran-2(3H)-one (1.78 g, 0.0153 mol) and 3,4-dihydro-2H-pyran (2.62 g, 0.0312 mol, Alfa) in 40 mL of CH2Cl2 was added PPTS (0.391 g, 0.00156 mol, Aldrich) slowly. After stirring at rt overnight, the reaction mixture was quenched with 5 mL of water. The mixture was extracted with EtOAc (50 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give pale yellow oil. The crude product was purified by a silica gel column chromatography (3:1 (v/v) petroleum ether/EtOAc) to afford the title compound as colorless oil (2.7 g, 88%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08293897B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-0f6a1f6bb802412490a79a9b6404c14c |
| Source note | uspto-grants-2012_10 |