HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 4-Hydroxy-4-pyrimidin-2-yl-cyclohexanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 8-Pyrimidin-2-yl-1,4-dioxa-spiro[4.5]decan-8-ol | HCID 59017433 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Hydroxy-4-pyrimidin-2-yl-cyclohexanone | HCID 59017430 | 49.3% |
Reaction Steps
To the product from step A (190 mmol, 44 g) in THF (200 mL) was added HCl solution (300 mmol, 100 mL). The reaction was stirred over 2 days after which the reaction was washed using diethyl ether. The aqueous layer was then quenched using NaOH (50%) to obtain a pH of 11. The aqueous layer was extracted using EtOAc (6×300 mL). The organic layer was combined and dried over MgSO4 and concentrated in vacuo. The residue was purified via flash chromatography to afford the desired ketone (18 g, 49%). MS [M+H]+193.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08362003B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-2819325b687548b691b4595b4539d014 |
| Source note | uspto-grants-2013_01 |