HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 2-(4-(tert-Butyldimethylsilyloxy)butoxy)-3-chlorobenzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol | HCID 186403 | — |
| Reactant | 3-Chloro-2-hydroxybenzaldehyde | HCID 519651 | — |
| Reactant | Di-tert-butyl diazene-1,2-dicarboxylate | HCID 6034084 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(4-(tert-Butyldimethylsilyloxy)butoxy)-3-chlorobenzaldehyde | HCID 86653468 | 25% |
Reaction Steps
To 3-chloro-2-hydroxybenzaldehyde (313 mg, 2 mmol) in tetrahydrofuran (4 mL) was added 4-(tert-butyldimethylsilyloxy)butan-1-ol (409 mg, 2 mmol), triphenylphosphine (524 mg, 2 mmol), and (E)-di-tert-butyl diazene-1,2-dicarboxylate (460 mg, 2 mmol). The mixture was stirred for 20 minutes and was purified by silica gel column chromatography eluting with hexanes and ethyl acetate (4:1) to afford the titled compound (170 mg; 25%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846951B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-e14248c666b646bb9552482dd90aec97 |
| Source note | uspto-grants-2014_09 |