Triethylamine → HCID 19000411, compound

HRID 2260427Notes

Reaction equation

HRID 2260427 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[C:9]([C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>O1CCCC1>[CH3:12][C:9]([C:13]1[CH:14]=[CH:15][C:16]([S:19][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2=[O:8])=[CH:17][CH:18]=1)([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 132032-ChlorocyclohexanoneHCID 754544-Tert-Butylbenzenethiol

Product 1

HCID 19000411HCID 19000411, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chlorocyclohexanone (6.1 g, 0.046 moles) in tetrahydrofuran (250 ml) cooled to +5° C. by an ice bath was added 4-t-butyl-thiophenol (6.6 g, 0.040 moles). After stirring for 15 minutes, triethylamine (13 ml) was added. The ice bath was removed and the mixture was stirred at room temperature for 60 hours. The mixture was filtered to remove a white solid. The filtrate was concentrated to an oil, and the product was purified by silica gel chromatography to give a white solid which was recrystallized from hexane (DSC 64.25° C.). The structure was supported by NMR and Ir.

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture was stirred at room temperature for 60 hours
  3. filtrationThe mixture was filtered
  4. customto remove a white solid
  5. concentrationThe filtrate was concentrated to an oil
  6. customthe product was purified by silica gel chromatography
  7. customto give a white solid which
  8. customwas recrystallized from hexane (DSC 64.25° C.)

Sources & evidence

ORD record
ord-98f8774332b14dd0898bffa689c089d4
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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