Thionyl Chloride → 2-[Chloro(cyclohexyl)methyl]-3,5-dimethyl-1-benzofuran

HRID 2091127Notes

Reaction equation

HRID 2091127 reaction equation
[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:12]=3[C:13]=2[CH3:14])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:22])=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:22][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[O:10][C:11]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:12]=2[C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66777213Cyclohexyl(3,5-dimethyl-1-benzofuran-2-yl)methanol

Product 1

HCID 667790612-[Chloro(cyclohexyl)methyl]-3,5-dimethyl-1-benzofuranYield 93%

Reagents, catalysts & solvents 1

HCID 22007288Pyridine tolueneSolvent

Procedure

To a solution (20 mL) of cyclohexyl(3,5-dimethyl-1-benzofuran-2-yl)methanol (1.13 g) synthesized above in toluene pyridine (424 μL) and thionyl chloride (382 μL) were added, and the mixture was stirred at room temperature for 5 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 (1.12 g, 93%) as a yellow oil.

Workup

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

Sources & evidence

ORD record
ord-e0004fd7f0704935826f02cf4b2ef97c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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