Thionyl Chloride → HCID 66778915, compound

HRID 2091122Notes

Reaction equation

HRID 2091122 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)O)=[C:7]([CH3:18])[C:6]=2[CH:19]=1.S(Cl)([Cl:22])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([Cl:22])[CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[C:7]([CH3:18])[C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66778911HCID 66778911, compound

Product 1

HCID 66778915HCID 66778915, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution (10 mL) of (5-chloro-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methanol (518 mg) synthesized above in toluene was added thionyl chloride (163 μL), and the mixture was stirred at 100° C. 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 (553 mg, quantitative) 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
  6. customto give the title object compound (553 mg, quantitative) as a pale-yellow oil

Sources & evidence

ORD record
ord-847bb386c41d4ecd850e2517b345a019
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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