Pyridine → 2-(1-Chloro-3-methylbutyl)-5-methoxy-3-methyl-1-benzofuran

HRID 2091132Notes

Reaction equation

HRID 2091132 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11](O)[CH2:12][CH:13]([CH3:15])[CH3:14])=[C:8]([CH3:17])[C:7]=2[CH:18]=1.N1C=CC=CC=1.S(Cl)([Cl:27])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:27][CH:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][C:7]=2[C:8]=1[CH3:17])[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 667777751-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutan-1-ol

Product 1

HCID 667782182-(1-Chloro-3-methylbutyl)-5-methoxy-3-methyl-1-benzofuranYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (10 mL) of 1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutan-1-ol (761 mg) synthesized above in toluene were added pyridine (297 μL) and thionyl chloride (268 μL), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (769 mg, 94%) as a brown oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f894c2d06abe48b0944b97c5cb90df45
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…