Lithium Hydroxide → 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH:11]=O.C([C:19]1[CH:37]=[CH:36][CH:35]=[CH:34][C:20]=1[C:21]([CH2:32][CH3:33])(CC)OP(CC([O-])=O)(O)=O)C.[Li+].[OH-:39].C1C[O:43][CH2:42][CH2:41]1>>[CH2:42]([O:43][C:33](=[O:39])[C:32]([CH2:21][C:20]1[CH:19]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[CH:11][C:7]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([Cl:1])[CH:15]=[C:14]([Cl:16])[CH:13]=2)[CH:10]=[CH:9][N:8]=1)[CH3:41]Participants
5
Procedure
To a solution of 1-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde (see Example 2) (0.59 g, 2.33 mmol) and triethyl-2-benzylphosponoacetate (0.81 g, 2.58 mmol) (prepared according to J. Med. Chem. 1993, 36, 87-94) in dry THF (3 mL) was added LiOH (62 mg, 2.58 mmol). The mixture was stirred for 14 h at ambient temperature then partitioned with water (20 mL) and EtOAc (40 mL). The organic layer was collected, washed with brine, dried over MgSO4 and concentrated in vacuo. The material was purified by column chromatography (silica gel, 100% diethyl ether) to provide 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester (0.41 g, 42%) as a colorless oil: ESI MS m/z 415 [C22H20Cl2N2O2+H]+.
Workup
- customthen partitioned with water (20 mL) and EtOAc (40 mL)
- customThe organic layer was collected
- washwashed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe material was purified by column chromatography (silica gel, 100% diethyl ether)
Sources & evidence
- ORD record
- ord-df6becb3a5174f7aad0f53a2011fdd05
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572921B2
Reaction notes
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