Sodium hydride → 1-[4-[[2-(Cyclooctyloxy)ethyl]thio]phenyl]ethanone

HRID 2225765Notes

Reaction equation

HRID 2225765 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:18][CH2:19][O:20][CH:21]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)(=O)=O>CN(C)C=O.O>[CH:21]1([O:20][CH2:19][CH2:18][S:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 47131801-(4-Sulfanylphenyl)ethan-1-oneHCID 190043182-(Cyclooctyloxy)ethyl methanesulfonate

Product 1

HCID 190044781-[4-[[2-(Cyclooctyloxy)ethyl]thio]phenyl]ethanoneYield 70.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 1-(4-mercaptophenyl)ethanone (0.76 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.218 g), stirred for 20 minutes and treated with 2-(cyclooctyloxy)ethyl methanesulfonate (1.25 g). The mixture was heated at 60° C. overnight, cooled, diluted with water, extracted twice with dichloromethane, and the organic layers were washed with water. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give crude material which was purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4) to provide 1.08 g of 1-[4-[[2-(cyclooctyloxy)ethyl]thio]phenyl]ethanone as a colorless oil.

Workup

  1. temperaturecooled
  2. extractionextracted twice with dichloromethane
  3. washthe organic layers were washed with water
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude material which
  8. customwas purified by HPLC (dichloromethane-hexane-ethyl acetate; 48:48:4)

Sources & evidence

ORD record
ord-beef348d17884277a7a676c30781b88a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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