HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonamide → 1-Propanone, 2-hydroxy-1-phenyl-, (2R)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | HCID 10377349 | HCID 10377349 | — |
| Reactant | 1,4-Bis(dihydroquinidine)phthalazine | HCID 11217202 | — |
| Solvent | 2-Methylpropan-2-ol--water (1/1) | HCID 71401949 | — |
| Product | 1-Propanone, 2-hydroxy-1-phenyl-, (2R)- | HCID 11804935 | 80% |
Reaction Steps
Compound 10b was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-phenprop-1-enyloxy)dimethylsilane (9b, 7.2 g, 0.029 mol), AD-mix-β (40.7 g), and CH3SO2NH2 (2.8 g, 0.0294 mol) in tert-butyl alcohol-water (110 mL:110 mL) The reaction was quenched with sodium sulfite (29.1 g). After purification, 2.49 g (80%) of the title product was isolated: [α]20D +84.9° (c 1.6, CHCl3); 1H NMR (CDCl3) δ 7.96-7.90 (m, 2H), 7.66-7.58 (m, 1H), 7.54-7.47 (m, 2H), 5.23-5.12 (m, 1H), 3.84 (d, 1H, J=6.3 Hz), 1.45 (d, 3H, J=7.05 Hz); 13C NMR (CDCl3) δ 202.4, 134.0, 133.4, 128.9, 128.7, 69.3, 22.3. C9H10O2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906908B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-3f29cbd822fd4d2d8f6e3b780afed32e |
| Source note | uspto-grants-2014_12 |