Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexanone | HCID 7967 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | 5'-Bromo-2'-hydroxyacetophenone | HCID 95991 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 10541879 | HCID 10541879 | 82% |
Reaction Steps
In a 50 mL round bottom flask was added 1-(5-bromo-2-hydroxyphenyl)ethanone (2.0 g, 9.3 mmol), followed by cyclohexanone (0.96 mL, 9.3 mmol). MeOH (20 mL) was added to give a clear solution followed by pyrrolidine (1 mL). A condenser was attached to the flask, and the resulting solution was heated at 60° C. overnight. MeOH was removed and the residue was redissolved in EtOAc (30 mL), washed with 1 N NaOH (10 mL) and 1 N HCl (10 mL), and then dried over Na2SO4. Solvent was removed in vacuo to give 6-bromospiro[chroman-2,1′-cyclohexan]-4-one (2.25 g, 82%), which is used for the next step without purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921359B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-a137217bc7074193bc106e4228993be3 |
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| Source note | uspto-grants-2014_12 |
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