Pyridine → 2-{4-[Chloro(cyclohexyl)methyl]-5-ethylthiophen-2-yl}-1,3-dioxolane

HRID 1877257Notes

Reaction equation

HRID 1877257 reaction equation
[CH:1]1([CH:7]([C:9]2[CH:13]=[C:12]([CH:14]3[O:18][CH2:17][CH2:16][O:15]3)[S:11][C:10]=2[CH2:19][CH3:20])O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)([Cl:29])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:29][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[O:18][CH2:17][CH2:16][O:15]2)[S:11][C:10]=1[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68515315Cyclohexyl[5-(1,3-dioxolan-2-yl)-2-ethylthiophen-3-yl]methanol

Product 1

HCID 685143042-{4-[Chloro(cyclohexyl)methyl]-5-ethylthiophen-2-yl}-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclohexyl[5-(1,3-dioxolan-2-yl)-2-ethylthiophen-3-yl]methanol (3.00 g) synthesized above in toluene (60 mL) were added pyridine (979 μL) and thionyl chloride (883 μL) at 0° C., and the mixture was stirred at 0° C. for 1.5 hr, and then at room temperature for 30 min. 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 compound (3.28 g, quantitative) as a pale-yellow oil.

Workup

  1. waitat room temperature for 30 min
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af81887c62fc4ef085d28a824ce4ad52
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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