Water → Ethyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate

HRID 573297Notes

Reaction equation

HRID 573297 reaction equation
[CH3:1][C:2]1([CH3:34])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]4[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=4[N:18]=3)=O)=[CH:11][CH:10]=2)[O:3]1.[H-].[Na+].[OH2:37].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[CH3:1][C:2]1([CH3:34])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([C:17]3[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]4[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=4[N:18]=3)=[CH:39][C:40]([O:41][CH2:42][CH3:38])=[O:37])=[CH:11][CH:10]=2)[O:3]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86688959[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)methanone

Product 1

HCID 131732831Ethyl 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)acrylate

Procedure

[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)methanone (1.0 g) was added to a solution of triethyl phosphonoacetate (0.498 mL) and NaH (60% in oil, 0.109 g) in THF (10 mL) at 0° C. The mixture was stirred at room temperature under a dry atmosphere for 1 h. The mixture was poured into water at room temperature and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (1.0 g).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

Sources & evidence

ORD record
ord-542e03d53c804455bbaae150a31af284
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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