Thionyl Chloride → HCID 66777149, compound

HRID 2090995Notes

Reaction equation

HRID 2090995 reaction equation
[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[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:21])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:21][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][CH:16]=[CH:15][C:12]=2[C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66778623HCID 66778623, compound

Product 1

HCID 66777149HCID 66777149, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of cyclohexyl(3-methyl-1-benzofuran-2-yl)methanol (843 mg) synthesized above and toluene (20 mL) was added thionyl chloride (256 μL), and the mixture was stirred at room temperature for 2.5 hr and at 50° C. for 1.5 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, 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 (862 mg, 95%) as a yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe 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-ccb6f6d5d3d94f9eb8a4234b7c167d39
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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