Methanol → HCID 21097347, compound

HRID 1350691Notes

Reaction equation

HRID 1350691 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-a6eaba869e3b41ecbe4a1ca2954cae38
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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