Water → 2-(1-Methyl-5-trimethylsilanylethynyl-1H-imidazol-2-yl)-propan-2-ol

HRID 2109202Notes

Reaction equation

HRID 2109202 reaction equation
[CH3:1][Mg+].[Br-].CC[O:6][CH2:7][CH3:8].C(OC([C:14]1[N:15]([CH3:25])[C:16]([C:19]#[C:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][N:18]=1)=O)C.O>C1COCC1>[CH3:25][N:15]1[C:16]([C:19]#[C:20][Si:21]([CH3:22])([CH3:24])[CH3:23])=[CH:17][N:18]=[C:14]1[C:7]([OH:6])([CH3:8])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 588614711-methyl-5-trimethylsilanylethynyl-1H-imidazole-2-carboxylic acid ethyl esterHCID 178418689HCID 178418689, compound

Product 1

HCID 210972522-(1-Methyl-5-trimethylsilanylethynyl-1H-imidazol-2-yl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.67 mL of 3M MeMgBr in ether (2.0 mmol) was added to a stirring 0° C. solution of 200 mg of 1-methyl-5-trimethylsilanylethynyl-1H-imidazole-2-carboxylic acid ethyl ester (0.80 mmol) in 5 mL of THF over 15 min. The mixture was allowed to warm to rt and stirred overnight. Water (20 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine and dried with MgSO4, filtered, concentrated and chromatographed (10-100 EtOAc in hexanes) to give 2-(1-methyl-5-trimethylsilanylethynyl-1H-imidazol-2-yl)-propan-2-ol as a yellow oil (110 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (10-100 EtOAc in hexanes)

Sources & evidence

ORD record
ord-46569abe983744f08ef2a1f72b9c01aa
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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