Thionyl Chloride → HCID 68514363, compound

HRID 1877204Notes

Reaction equation

HRID 1877204 reaction equation
[CH:1]1([CH:7](O)[C:8]2[CH:9]=[C:10]([C:15]3(O)[CH2:20][CH2:19][S:18][CH2:17][CH2:16]3)[S:11][C:12]=2[CH2:13][CH3:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:25])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:25][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8]1[CH:9]=[C:10]([C:15]2[CH2:20][CH2:19][S:18][CH2:17][CH:16]=2)[S:11][C:12]=1[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68511594HCID 68511594, compound

Product 1

HCID 68514363HCID 68514363, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-{4-[cyclohexyl(hydroxy)methyl]-5-ethylthiophen-2-yl}tetrahydro-2H-thiopyran-4-ol (532 mg) synthesized in Example 85 (3) in toluene (10 mL) was added thionyl chloride (137 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 compound (491 mg, 92%) as a 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-9c1f1b6639c44b2d81828ec32c224ce2
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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