HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 14932533, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol | HCID 186403 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 14932533 | HCID 14932533 | 81.4% |
Reaction Steps
To a solution of 4-(t-butyldimethylsilyloxy)-1-butanol (2.8 g, 13.7 mmol) in dichloromethane (30 ml) were added triethyamine (3.83 ml, 27.4 mmol) and p-toluenesulfonyl chloride (2.88 g, 15.1 mmol) at 0° C., which was then stirred at the same temperature for 2 hours. After the reaction was completed, water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give the title compound (4.0 g, yield: 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07074819B2 |
| Source dataset | uspto-grants-2006_07 |
| ORD ID | ord-2235ddf34e06478eb42a7b73609e4d6d |
| Source note | uspto-grants-2006_07 |