Ethanol → 4-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690739Notes

Reaction equation

HRID 1690739 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH2:30]([OH:32])[CH3:31]>>[CH2:30]([O:32][CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1)[CH3:31]

Participants

4

Reactant 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 669066914-(5-Chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Product 1

HCID 577810774-(5-Ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Procedure

To a solution of 4-(5-chloromethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.150 g, 0.516 mmol), prepared as described in Example 18, in anhydrous ethanol (5 mL) is added diisopropylethyl amine (0.100 g, 0.77 mmol) and the mixture is stirred at reflux overnight. The mixture is purified by semi-preparative reverse phase HPLC to give 4-(5-ethoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 301.0 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.26 (s, 3 H), 1.29 (t, J=6.1 Hz, 3 H), 1.54 (s, 3 H), 3.62 (br. s, 2 H), 4.70 (br. s, 2 H), 5.59 (s, 1 H), 7.02 (s, 1 H), 7.29 (br. s, 1 H), 7.52 (d, J=7.8 Hz, 1 H), 7.63 (td, J=7.8, 1.3 Hz, 1 H), 7.74 (td, J=7.6, 1.3 Hz, 1 H), 8.21 (dd, J=7.8, 1.3 Hz, 1H).

Workup

  1. temperatureat reflux overnight
  2. customThe mixture is purified by semi-preparative reverse phase HPLC

Sources & evidence

ORD record
ord-be7afdd112e14dc99f6147ddb0ea255c
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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