Cyclohexanethiol → Ethyl 3-(cyclohexylthio)benzoate

HRID 1967555Notes

Reaction equation

HRID 1967555 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH:13]1([SH:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH:13]1([S:19][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 15290CyclohexanethiolHCID 81531DiisopropylethylamineHCID 143542Ethyl 3-iodobenzoateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 66872472Ethyl 3-(cyclohexylthio)benzoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 3-iodobenzoate (5.00 g) was dissolve din dioxane (100 mL), and cyclohexanethiol (2.32 mL), N,N-diisopropylethylamine (6.29 mL), Xantphos (2.09 g) and Pd2(dba)3 (1.66 g) were added thereto in that order, and stirred in a nitrogen atmosphere at 100° C. for 7 hours. After left cooled, ethyl acetate was added to it, then washed with water ad saturated brine in that order, and dried with sodium sulfate. The drying agent was removed through filtration, the solvent was evaporated off under reduced pressure, and the residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 25%, gradient) to give the intended compound (5.11 g) as an orange oil.

Workup

  1. additionwere added
  2. waitAfter left
  3. temperaturecooled
  4. washwashed with water ad saturated brine in that order
  5. dry with materialdried with sodium sulfate
  6. customThe drying agent was removed through filtration
  7. customthe solvent was evaporated off under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 25%, gradient)

Sources & evidence

ORD record
ord-8141930db92b44d2a4e5718b805c995b
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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