4-[5-(2-Methoxy-vinyl)-imidazole-1-yl]-3,3-dimethyl-isochroman-1-one → 4-[5-(2-Methoxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one

HRID 1690731Notes

Reaction equation

HRID 1690731 reaction equation
[CH3:1][O:2][CH:3]=[CH:4][C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[O:12][C:11]2([CH3:22])[CH3:21])[CH:8]=[N:7][CH:6]=1>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:9]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:20])[O:12][C:11]2([CH3:22])[CH3:21])[CH:8]=[N:7][CH:6]=1

Participants

4

Reactant 1

HCID 669060214-[5-(2-Methoxy-vinyl)-imidazole-1-yl]-3,3-dimethyl-isochroman-1-one

Product 1

HCID 577811104-[5-(2-Methoxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[5-(2-methoxy-vinyl)-imidazole-1-yl]-3,3-dimethyl-isochroman-1-one (0.110 g, 0.37 mmol) in methanol (5 mL) is added Pd/C (0.020 g). The reaction vessel is flushed with hydrogen gas and stirred under balloon pressure for 72 h. The mixture is filtered, and the filtrate concentrated in vacuo to give a residue which is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-[5-(2-methoxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one as a white solid; HRMS (ESI) m/z 301.1555 [(M+H)+: Calcd for C17H20N2O3: 301.1552]; 1H NMR (400 MHz, MeOD) δ ppm 1.25 (s, 3 H), 1.56 (s, 3H), 3.13 (br. s, 2 H), 3.45 (br. s, 3 H), 3.70-3.79 (m, 2 H), 5.71 (s, 1 H), 6.90 (s, 1 H), 7.15 (br. s, 1 H), 7.52 (d, J=7.6 Hz, 1 H), 7.60-7.72 (m, 1 H), 7.74-7.86 (m, 1 H), 8.24 (dd, J=7.8, 1.5 Hz, 1 H)

Workup

  1. customThe reaction vessel is flushed with hydrogen gas
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a residue which
  5. customis purified by silica gel chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-d097108f333d44ecaf82db927c36228f
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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