4-(5-But-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one → 4-(5-Butyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690729Notes

Reaction equation

HRID 1690729 reaction equation
[CH:1]([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)=[CH:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([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([CH3:21])[CH3:22])[CH:8]=[N:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 669064414-(5-But-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Product 1

HCID 577810794-(5-Butyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(5-but-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.110 g, 0.37 mmol) in methanol (2 mL) is added Pd/C (0.020 g). The reaction vessel is flushed with hydrogen gas and stirred under balloon pressure overnight. The mixture is filtered and the filtrate concentrated in vacuo to give a residue which is purified by semi-preparative reverse phase HPLC to give 4-(5-butyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 299.1 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.02 (br. s, 3 H), 1.22 (s, 3 H), 1.53 (br. s, 5 H), 1.77 (br. s, 2 H), 2.81 (br. s, 2 H), 5.54 (br. s, 1 H), 6.82 (s, 1H), 7.19 (br. s, 1 H), 7.39 (d, J=7.3 Hz, 1 H), 7.60-7.67 (m, 1 H), 7.71-7.78 (m, 1 H), 8.21 (d, J=7.8 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 semi-preparative reverse phase HPLC

Sources & evidence

ORD record
ord-e3da2c8130e645fc9c8f1b2583a5f9c5
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

Loading…