p-Chlorothiophenol → HCID 178501293, compound

HRID 2370081Notes

Reaction equation

HRID 2370081 reaction equation
O[C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C@H:2]2[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 4622928CyanomethylenetributylphosphoraneHCID 178501284HCID 178501284, compound

Product 1

HCID 178501293HCID 178501293, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl cis-4-hydroxycyclohexanecarboxylate (500 mg, 3.16 mmol) in toluene (30 mL), 4-chlorobenzenethiol (457 mg, 3.16 mmol) and cyanomethylenetributylphosphorane (915 mg, 3.16 mmol) were added, and the resulting mixture was stirred at 100° C. for 2 hours. Then, the residue obtained by distilling off the solvent in the reaction solution under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 85:15 (v/v)), whereby the title compound was obtained as an oil (206 mg, yield: 26%).

Workup

  1. customThen, the residue obtained
  2. distillationby distilling off the solvent in the reaction solution under reduced pressure
  3. customwas purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 85:15 (v/v)), whereby the title compound

Sources & evidence

ORD record
ord-dee52249687342d4850d657cfb8cb645
Source dataset
uspto-grants-2014_04
Patent number
US08710060B2

Reaction notes

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