Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | TBAF tetrahydrofuran | HCID 11078149 | — |
| Reactant | HCID 86702586 | HCID 86702586 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86702585 | HCID 86702585 | 58% |
Reaction Steps
To a tetrahydrofuran (74 mL) solution of the compound 9 (7.3 g) was added a 1 M tetrabutylammonium fluoride/tetrahydrofuran solution (27 mL), and the mixture was stirred for 3 hours. The reaction liquid was diluted with ethyl acetate (380 mL), washed with water (740 mL) and a saturated saline (380 mL). Further the aqueous layer was extracted with ethyl acetate (100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1). The resulting compound was purified again by silica gel column chromatography (dichloromethane:ethyl acetate=4:1→ethyl acetate) to obtain a titled compound (3.24 g) having the following physical property values.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150537B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-b7491afb40ec4033a64b1d1e814d7204 |
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| Source note | uspto-grants-2015_10 |
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