Methanol → HCID 21097347, compound

HRID 2109196Notes

Reaction equation

HRID 2109196 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][N:4]=[C:3]1[S:9][CH3:10].[CH3:11]O>C([O-])([O-])=O.[K+].[K+]>[C:7]([C:6]1[N:2]([CH3:1])[C:3]([S:9][CH3:10])=[N:4][CH:5]=1)#[CH:11]

Participants

4

Reactant 2

HCID 887MethanolHCID 638695HCID 638695, compound

Product 1

HCID 21097347HCID 21097347, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent2×

Procedure

To a mixture of 850 mg (5.44 mmol) of 3-methyl-2-methylsulfanyl-3H-imidazole-4-carbaldehyde and 1.34 g (7.00 mmol) of dimethyl 2-oxo-1-diazopropylphosphinate in 15 mL of MeOH was added 1.52 g (11.0 mmol) of K2CO3. The mixture was stirred at room temperature for 28 hours. The mixture was diluted with saturated K2CO3 (10 mL) and and extracted with CH2Cl2 (3×75 mL). The combined extracts were dried over MgSO4, concentrated, and chromatographed (0 to 100% EtOAc in hexanes) to give the 5-ethynyl-1-methyl-2-methylsulfanyl-1H-imidazole (600 mg, 72%) as a colorless liquid.

Workup

  1. extractionextracted with CH2Cl2 (3×75 mL)
  2. dry with materialThe combined extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customchromatographed (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-33f2407f7d4246dd812a5ac8fe0cfbdf
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

Loading…