Iodine → HCID 67399749, compound

HRID 70508

Reaction equation

HRID 70508 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1.[Mg].[CH:14]1([C:17]2[CH:18]=[CH:19][C:20]([CH:25]=[O:26])=[N:21][C:22]=2[O:23][CH3:24])[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([C:17]2[CH:18]=[CH:19][C:20]([CH:25]([C:4]3[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=3)[OH:26])=[N:21][C:22]=2[O:23][CH3:24])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 807IodineHCID 685234-BromophenetoleHCID 5462224MagnesiumHCID 86657999HCID 86657999, compound

Product 1

HCID 67399749HCID 67399749, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A small amount of iodine was added to a suspension of 1-bromo-4-ethoxybenzene (484 μL) and magnesium (82.3 mg) in THF at room temperature in a nitrogen atmosphere, and the mixture was stirred at 50° C. for one hour. The reaction solution was returned to room temperature and a solution of 5-cyclopropyl-6-methoxypyridine-2-carbaldehyde (300 mg) in tetrahydrofuran (1 mL) was added, followed by stirring at 50° C. for one hour. Tetrahydrofuran was concentrated under reduced pressure and a saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was filtered through diatomaceous earth, and then the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→9:1) to give (5-cyclopropyl-6-methoxypyridin-2-yl)(4-ethoxyphenyl)methanol as a yellow oil (438 mg, 86%).

Workup

  1. customwas returned to room temperature
  2. stirringby stirring at 50° C. for one hour
  3. concentrationTetrahydrofuran was concentrated under reduced pressure
  4. additiona saturated ammonium chloride solution was added
  5. extractionfollowed by extraction with ethyl acetate
  6. filtrationThe organic layer was filtered through diatomaceous earth
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→9:1)

Sources & evidence

ORD record
ord-1d8f5338754f45f0bb6e0781d35a07a1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

Loading…