HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → Tert-butyl {3-[4-(chloromethyl)-3-methoxyphenoxy]propoxy}dimethylsilane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | (4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-methoxyphenyl)methanol | HCID 68747805 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | Tert-butyl {3-[4-(chloromethyl)-3-methoxyphenoxy]propoxy}dimethylsilane | HCID 123781615 | 111.8% |
Reaction Steps
Methanesulfonyl chloride (4.02 mL) was added to the mixture of the product from step (ii) (8.47 g), diisopropylethylamine (13.4 mL) and lithium chloride (3.29 g) in THF (105 mL) at RT and stirred for 40 mins. The mixture was diluted with water and brine, and extracted with EtOAc. The combined organic solutions were washed with brine, dried and concentrated to give 10.0 g of the subtitle compound as a yellow oil; 1H NMR: 7.23 (1H, dd), 6.44-6.49 (2H, m), 4.63 (2H, s), 4.06 (2H, t), 3.85 (3H, s), 3.79 (2H, t), 1.94-2.02 (2H, m), 0.89 (9H, s), 0.04 (6H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376398B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-93fc405323ad468e9c033d5c7fed2397 |
| Source note | uspto-grants-2016_06 |