HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Fluorophenol → 4-(5-(tert-butyldimethylsilyloxy)-2-fluoro-alpha-hydroxybenzyl)-N,N-diethylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Fluorophenol | HCID 9707 | — |
| Reactant | tert-Butyl(2-fluorophenoxy)dimethylsilane | HCID 597214 | — |
| Reactant | N,N-diethyl-4-formylbenzamide | HCID 10954698 | — |
| Reactant | CID 53628100 | HCID 178418400 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(5-(tert-butyldimethylsilyloxy)-2-fluoro-alpha-hydroxybenzyl)-N,N-diethylbenzamide | HCID 54114191 | 34% |
Reaction Steps
tert-Butyldimethylsilyl 2-fluorophenyl ether (2.73 g, 12 mmol), prepared from 2-fluorophenol by the method in Example 1, was treated with sec-butyllithium (11 mL of 1.1M solution in cyclohexane) and 4-formyl-N,N -diethylbenzamide, (2.46 g, 12 mmol) from Example 11, by the procedure described in Example 29. Chromatography on silica gel with 1% methanol in dichloromethane gave 1.77 g (34%) of 4-(5-(tert-butyidimethylsilyloxy)-2-fluoro-α-hydroxybenzyl)-N,N-diethylbenzamide as a yellow oil that crystallized on standing.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05658908 |
| Source dataset | uspto-grants-1997_08 |
| ORD ID | ord-ad0111c3fc5b49a9b471ef743a51984e |
| Source note | uspto-grants-1997_08 |