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

HRID 2101499
Notes
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Reaction equation

HRID 2101499 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 578014901-(3,5-dichloro-benzyl)-1H-imidazole-2-carbaldehydeHCID 131727578Triethyl-2-benzylphosponoacetate

Product 1

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

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

  1. customthen partitioned with water (20 mL) and EtOAc (40 mL)
  2. customThe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe material was purified by column chromatography (silica gel, 100% diethyl ether)

Sources & evidence

ORD record
ord-df6becb3a5174f7aad0f53a2011fdd05
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572921B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes