Ethylene Glycol → HCID 23294929, compound

HRID 1955285Notes

Reaction equation

HRID 1955285 reaction equation
[ClH:1].[C:2]1([C:8]2([C:15]([O:17][CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:38](O)[CH2:39][OH:40]>C1(C)C=CC=CC=1>[ClH:1].[C:2]1([C:8]2([C:15]([O:17][CH2:18][CH2:19][N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:22])[CH3:23])=[O:16])[CH2:9][CH2:10][C:11]3([O:40][CH2:39][CH2:38][O:14]3)[CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 23294901HCID 23294901, compound

Product 1

HCID 23294929HCID 23294929, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(Diisopropylamino)ethyl 1-phenyl-4-oxocyclohexanecarboxylate hydrochloride (3 mmol), prepared in Example 119, was refluxed for 4 h with p-toluenesulfonic acid (1.5 mmol) and ethyleneglycol (4 mmol) in toluene (50 mL) using a Dean-Stark trap. The reaction mixture was partitioned between Et2O and 2 M NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The residue was dissolved in Et2O and HCl (g)/Et2O was added. The amine salt was recrystallized from acetone/Et2O to yield 0.53 g (43%); mp 121-128° C.; 1H NMR (CD3OD) δ 1.25 (d, 12H), 1.72 (m, 4H), 2.13 (m, 2H), 2.47 (m, 2H), 3.35 (t, 2H), 3.59 (m, 2H), 3.93 (m, 4H), 4.42 (t, 2H), 7.26-7.47 (m, 5H).

Workup

  1. customThe reaction mixture was partitioned between Et2O and 2 M NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in Et2O
  5. additionHCl (g)/Et2O was added
  6. customThe amine salt was recrystallized from acetone/Et2O
  7. customto yield 0.53 g (43%)

Sources & evidence

ORD record
ord-b0324339928e4d23aa8295edb3f17c6b
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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