Diiodomethane → HCID 80463661, compound

HRID 1747516Notes

Reaction equation

HRID 1747516 reaction equation
[CH3:1][C:2](=[CH2:11])[CH:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].[CH2:12]([Zn]CC)C.ICI.[Cl-].[NH4+]>ClCCl.O>[CH3:11][C:2]1([CH:3]([C:5]2[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=2)[OH:4])[CH2:12][CH2:1]1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 17953062HCID 17953062, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 80463661HCID 80463661, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In dichloromethane (40.0 mL) was dissolved 2-methyl-1-(pyridin-3-yl)prop-2-en-1-ol (1.04 g, 6.95 mmol) obtained in Step 1. Diethylzinc (1.09 mol/L solution in n-hexane, 31.9 mL, 34.7 mmol) and diiodomethane (2.80 mL, 34.7 mmol) were added dropwise at −10° C. and the mixture was stirred at 0° C. for 2.5 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give (1-methylcyclopropyl)(pyridin-3-yl)methanol (888 mg, 78% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)

Sources & evidence

ORD record
ord-e9bfa090a04349da9abc414dd4b58df4
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

Loading…