HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | (4R,4aS,7R,7aR)-7-methoxy-2,2-dimethyl-4-vinyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one | HCID 49871274 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one | HCID 67241097 | — |
Reaction Steps
10 mL of TFA are added dropwise at 0° C. to a 100 mL round-bottomed flask containing 1.0 g of 30 (4.38 mmol), 10 mL of water and 14 mL of THF. The medium is allowed to return to RT and stirred overnight. The medium is then concentrated at reduced pressure at RT and 50 mL of water are added, and the mixture is frozen and freeze-dried. The freeze-dried product is impasted in heptane in the presence of a minimum amount of methanol, and after evaporation of the solvents, 778 mg of expected product 31 (white solid) are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07994161B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-166fd210f5344b15a6f81c90e95b9c23 |
| Source note | uspto-grants-2011_08 |