HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphate | HCID 21110492 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | Diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphate | HCID 17862563 | 83% |
Reaction Steps
To a solution of diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphate (4.41 g, 9.87 mmol) obtained from Example 27-(2) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1N tetrahydrofuran solution; 10 ml, 10 mmol), and the mixture was stirred at room temperature for 40 minutes. Water was added to the mixture, then the product was extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:1˜3:1) to afford the title compound (2.71 g, 83% yield) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07230023B2 |
| Source dataset | uspto-grants-2007_06 |
| ORD ID | ord-7b02223420fd4a368ea6ac2e0157d8bf |
| Source note | uspto-grants-2007_06 |