HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (Z)-tert-Butyl(1-(m-tolyl)prop-1-enyloxy)dimethylsilane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Butyrophenone | HCID 10315 | — |
| Reactant | tert-Butyldimethylsilyl trifluoromethanesulphonate | HCID 123564 | — |
| Reactant | 1-Chloro-3-[(1Z)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propen-1-yl]-benzene | HCID 11300561 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (Z)-tert-Butyl(1-(m-tolyl)prop-1-enyloxy)dimethylsilane | HCID 46838065 | 84% |
Reaction Steps
Compound 9e was synthesized by a procedure similar to that described for 9a using commercially available 3-methylpropiophenone (8e, 5.0 g, 0.033 mol), TBDMSOTf (8.5 mL, 36.1 mmol), and Et3N (7.5 mL) in CH2Cl2 (50 mL). After purification by column chromatography on silica gel, 7.45 g (84%) of 9e was isolated as colorless oil: 1H NMR (CDCl3) δ 7.31-7.24 (m, 2H), 7.23-7.17 (m, 1H), 7.10-7.05 (m, 1H), 5.22 (q, 1H, J=6.9 Hz), 2.37 (s, 3H), 1.76 (d, 3H, J=6.9 Hz), 1.03 (s, 9H), −0.03 (s, 6H); 13C NMR (CDCl3) δ 150.7, 140.1, 137.7, 128.4, 127.9, 126.8, 123.2, 105.9, 26.3, 21.8, 18.7, 12.1, −3.6. C16H26OSi.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906908B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-b96301f933764b21bc62bc296fbde524 |
| Source note | uspto-grants-2014_12 |