Thionyl Chloride → 3-[Chloro(cyclohexyl)methyl]-6-methoxy-2-methyl-1-benzofuran

HRID 2091431Notes

Reaction equation

HRID 2091431 reaction equation
[CH:1]1([CH:7]([C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=3[O:11][C:10]=2[CH3:20])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:23])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:23][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]=2[O:11][C:10]=1[CH3:20]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66778469HCID 66778469, compound

Product 1

HCID 667772013-[Chloro(cyclohexyl)methyl]-6-methoxy-2-methyl-1-benzofuranYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (10 mL) of cyclohexyl(6-methoxy-2-methyl-1-benzofuran-3-yl)methanol (499 mg) synthesized above in toluene was added thionyl chloride (159 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the 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 (530 mg, 99%) as a pale-yellow oil.

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a2e09809e434d70a269914811cf9fcf
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…