HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Potassium Sodium Tartrate | HCID 9357 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | 2-(t-Butyldimethylsilyl)-5-phenylsulfanylimidazole-1-sulfonic acid dimethylamide | HCID 54230476 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde | HCID 9995968 | — |
Reaction Steps
A solution of cyclohexenone (1) (2.88 g, 30 mmol) in hexanes at −78° C. was treated with DIBAL (30 mL, 1.0 M in cyclohexane). After 25 m, MeOH (7 mL) was added and the mixture was warmed to rt. A saturated solution of Rochelle's salt was added followed by dilution with ether (100 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated under vacuum. The product was purified by chromatography on SiO2 with 20% EtOAc:Hx to give a clear colorless alcohol 2, 2.0 g (68%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329369B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-38b613d9d7e748c4aadb3b9e972bb995 |
| Source note | uspto-grants-2001_12 |