Thionyl Chloride → HCID 63433147, compound

HRID 2090976Notes

Reaction equation

HRID 2090976 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)O)=[CH:2]1.S(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:20][CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH:2]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 61088367HCID 61088367, compound

Product 1

HCID 63433147HCID 63433147, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-benzothiophen-3-yl(cyclohexyl)methanol (2.32 g) synthesized above in toluene (25 mL) was added dropwise thionyl chloride (824 μL), and the mixture was stirred at room temperature for 4 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 (2.42 g, 97%) as an orange 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-e4e6a3b29b8a437bb83dccbd08cf9259
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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