Lithium Hydroxide → 2-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester

反応式

[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]

参加物

反応物 4

HCID 3939Lithium Hydroxide

HCID 8028Tetrahydrofuran

HCID 578014901-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehyde

HCID 131727578Triethyl-2-benzylphosponoacetate

生成物 1

HCID 688632652-benzyl-3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-acrylic acid ethyl ester収率 42%

実験手順

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]+.