Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylstannane | HCID 5948 | — |
| Reactant | HCID 19079050 | HCID 19079050 | — |
| Catalyst | Azobisisobutyronitrile | HCID 6547 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 19434456 | HCID 19434456 | 55.4% |
Reaction Steps
Dissolved 2-bromo-2-[6,11-dihydro-11-ethoxy-dibenz[b,e]oxepin-11-yl]-ethanol (14.34 g, 0.0395 mol) in 150 mL of dry toluene. Added tri-n-butyl tin hydride (17.24 g, 15.9 mL, 0.0592 mol) and AIBN (0.324 g, 0.00197 mol). Refluxed under a nitrogen atmosphere for 18 hours. Cooled to room temperature, and evaporated. Dissolved residue in 300 mL of acetonitrile, and washed with hexane to remove tin by-products. Dried acetonitrile solution with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane then 1:3 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 6.22 g (55% yield) of 2-[6,11-dihydro-11-ethoxydibenz[b,e]oxepin-11-yl]-ethanol as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05538986 |
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| Source dataset | uspto-grants-1996_07 |
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| ORD ID | ord-f0188ec914394c73a988da9d172cf04c |
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| Source note | uspto-grants-1996_07 |
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