HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrabutylammonium Fluoride → ethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (1S,1aS,6bR)-Ethyl-5-((tert-butyldimethylsilyl)oxy)-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate | HCID 131734886 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | ethyl (1S,1aS,6bR)-5-hydroxy-1a,6b-dihydro-1H-cyclopropa[b]benzofuran-1-carboxylate | HCID 89670235 | 57% |
Reaction Steps
Tetra-n-butylammonium fluoride (TBAF, 1M in THF, 4 mmol) was added dropwise to a solution of the product of Step A (7.3 g, crude) in THF (100 mL) at 0° C. The reaction was stirred at RT for 30 min. The mixture was concentrated and purified by column chromatography to afford the title compound as a solid (2.52 g, 57% for 2 steps, 72% ee).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09273046B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-a5a525f98fb04440b06e8e4a11ea08db |
| Source note | uspto-grants-2016_03 |