Methanol → 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde

HRID 1760476Notes

Reaction equation

HRID 1760476 reaction equation
[CH3:1][N:2]([CH3:25])[S:3]([N:6]1[C:10](SC2C=CC=CC=2)=[CH:9][N:8]=[C:7]1[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])(=[O:5])=[O:4].CC(C[AlH]CC(C)C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)[C:39]([O-])=[O:40].[Na+].[K+]>CCOCC>[CH3:25][N:2]([CH3:1])[S:3]([N:6]1[C:10]([CH:39]=[O:40])=[CH:9][N:8]=[C:7]1[Si:18]([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:19])[CH3:20])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 542304762-(t-Butyldimethylsilyl)-5-phenylsulfanylimidazole-1-sulfonic acid dimethylamide

Product 1

HCID 99959681-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe product was purified by chromatography on SiO2 with 20% EtOAc

Sources & evidence

ORD record
ord-7371b4a4bb0e45ce9989fb7b9218f287
Source dataset
uspto-grants-2005_01
Patent number
US06841684B2

Reaction notes

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