Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 9H-fluorene, 9-phenyl- | HCID 13091 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22117513 | HCID 22117513 | — |
Reaction Steps
To a solution of 9-phenylfluorene (13.6 mmol) in THF (40 mL) is added nBuLi (1.2 eq) dropwise at 0° C. under an argon atmosphere. The resulting mixture is stirred at 0° C. for 30 min. Paraformaldehyde (1.2 eq) is added in one portion, and the resulting mixture is allowed to stir at room temperature overnight. The reaction mixture is quenched with saturated NH4Cl solution. The resulting mixture is extracted with EtOAc. The EtOAc layer is dried (Na2SO4) and concentrated in vacuo. The concentrate is purified by flash chromatography on silica gel eluting with hexanes-ethyl acetate to isolate the alcohol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06162824 |
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| Source dataset | uspto-grants-2000_12 |
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| ORD ID | ord-0d578cf4578b4649b981cec4ebadadad |
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| Source note | uspto-grants-2000_12 |
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