1,1'-Carbonyldiimidazole → Methyl [4-(5-imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate

HRID 844809Notes

Reaction equation

HRID 844809 reaction equation
OC1[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[C:27]([N:34]1[CH:38]=[CH:37][N:36]=[CH:35]1)(N1C=CN=C1)=O>C1COCC1>[N:34]1([CH:27]2[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]3[CH:7]=[C:6]([C:14]#[C:15][C:16]4[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=4)[CH:5]=[CH:4][C:3]2=3)[CH:38]=[CH:37][N:36]=[CH:35]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86585937Methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate2×

Product 1

HCID 86585938Methyl [4-(5-imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetateYield 31.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl [4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate (Compound 135, 140.0 mg, 0.40 mmol) and carbonyldiimidazole (136.0 mg, 0.84 mmol) in 5 mL THF was heated to 65° C. for 48 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in Et2O and washed with 5% aqueous NaOH, H2O, and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. Column chromatography (5% MeOH—CH2Cl2) afforded 50.0 mg (31%) of the title compound as a colorless solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in Et2O
  3. washwashed with 5% aqueous NaOH, H2O, and saturated aqueous NaCl
  4. dry with materialbefore being dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-051f7b3b50fa45308119ca282da5c879
Source dataset
uspto-grants-2002_04
Patent number
US06380256B1

Reaction notes

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