Thionyl Chloride → 4-{4-[chloro(cyclohexyl)methyl]-5-ethylthiophen-2-yl}tetrahydro-2H-thiopyran

HRID 1877224Notes

Reaction equation

HRID 1877224 reaction equation
[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][S:17][CH2:16][CH2:15]3)[S:11][C:10]=2[CH2:20][CH3:21])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:24][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[CH:13]=[C:12]([CH:14]2[CH2:19][CH2:18][S:17][CH2:16][CH2:15]2)[S:11][C:10]=1[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68511464cyclohexyl[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol

Product 1

HCID 685121934-{4-[chloro(cyclohexyl)methyl]-5-ethylthiophen-2-yl}tetrahydro-2H-thiopyranYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclohexyl[2-ethyl-5-(tetrahydro-2H-thiopyran-4-yl)thiophen-3-yl]methanol (1.91 g) synthesized above in toluene (20 mL) was added thionyl chloride (516 μL), and the mixture was stirred at room temperature for 1.5 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 (1.91 g, 95%) 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-46923e72ad084ff591043bf01a3e0277
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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