4-Methylbenzenethiol → HCID 12922226, compound

HRID 2371857Notes

Reaction equation

HRID 2371857 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][C:7](C)([O-])C.[K+].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.C1(C2CCCCCC2)CCCCCC1>C(O)(C)(C)C>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH:1]2[CH2:2][CH2:3][CH2:7][CH2:6][CH:5]2[OH:4])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 78114-MethylbenzenethiolHCID 8028TetrahydrofuranHCID 141010BicycloheptaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 12922226HCID 12922226, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A 100 ml flask was flame dried, purged with dry nitrogen and fitted with a magnetic stirrer, heating mantle and condenser. Dry THF (25 ml), t-butanol (25 ml), potassium t-butoxide (0.700 g, 2.5 equiv.) and 4-methylthiophenol (1.0515 g, 3.0 equiv.) were added and the mixture was allowed to stir until all of the added solid had dissolved. 1,(R,S),2,(S,R),-4(R,S),4(R,S),5(R,S)-4,5-bis ((dipropylcarbamoylmethoxy)-4-oxa-[4.1.0]-bicycloheptane (1.030 g, 2.50 mmol) was added and the mixture was warmed and allowed to reflux for 72 hours. The reaction vessel was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in diethyl ether and extracted 4 times with saturated sodium carbonate and once with brine. The organic layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo. Pure product F was obtained by column chromatography of the residue with 100% ethyl acetate yielding pure 1,(R,S),2(R,S),4(R,S),5(R,S)-4,5 -bis(dipropylcarbamoyl)-methoxy)-2-(4-methyl thiophenoxy)-cyclohexanol, subreaction product 14, (0.423 g, 31%) as a viscous oil.

Workup

  1. temperatureA 100 ml flask was flame
  2. customdried
  3. custompurged with dry nitrogen
  4. customfitted with a magnetic stirrer
  5. temperatureheating mantle
  6. dissolutionhad dissolved
  7. temperaturethe mixture was warmed
  8. temperatureto reflux for 72 hours
  9. customthe solvent was removed in vacuo
  10. dissolutionThe residue was dissolved in diethyl ether
  11. extractionextracted 4 times with saturated sodium carbonate
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. filtrationfiltered
  14. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6f65396cca2e401ab0733b5126426121
Source dataset
uspto-grants-1992_03
Patent number
US05096832

Reaction notes

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