HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 1-(tert-Butyldimethylsilyloxy)-2-propanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Hydroxyacetone | HCID 8299 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Product | 1-(tert-Butyldimethylsilyloxy)-2-propanone | HCID 4124969 | 75% |
Reaction Steps
To a DCM (5 mL) solution of 1-hydroxypropan-2-one (500 mg, 6.8 mmol), DMAP (41 mg, 0.34 mmol) and Et3N (1.2 mL, 8.16 mmol) was added TBSCl (1.133 g, 7.5 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. Then the mixture was added water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (10/1) to give the title compound (950 mg, 75%). EDI-MS (M+1): 189. 1H NMR (300 MHz, CDCl3) δ 4.057 (s, 2H), 2.080 (s, 3H), 0.832 (s, 9H), 0.001 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08349849B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-331a42c68ba94391bafb6557b2377592 |
| Source note | uspto-grants-2013_01 |