Tetrahydrofuran → HCID 69070100, compound

HRID 2110026Notes

Reaction equation

HRID 2110026 reaction equation
[C:1]1([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][N:19]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:20]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:23]4[CH:33]=[CH:34][C:35]([CH:37]=[O:38])=[CH:36][C:22]=4[N:21]=3)[CH2:14][CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].O1CC[CH2:51][CH2:50]1>C([Mg]Br)C>[C:1]1([CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([CH2:18][N:19]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:20]3[N:24]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[C:23]4[CH:33]=[CH:34][C:35]([CH:37]([OH:38])[CH2:50][CH3:51])=[CH:36][C:22]=4[N:21]=3)[CH2:16][CH2:17]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 230689442-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboaldehyde

Product 1

HCID 69070100HCID 69070100, compound

Reagents, catalysts & solvents 1

HCID 178418443HCID 178418443, compoundSolvent

Procedure

After dissolving 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazole-5-carboaldehyde (86 mg, 0.131 mmol) in anhydrous tetrahydrofuran (1.2 ml) under a nitrogen stream, ethylmagnesium bromide (0.26 ml, 1M tetrahydrofuran solution) was added at 0° C., and the mixture was stirred at room temperature for 13 minutes. Saturated aqueous ammonium chloride was added, and extraction was performed with ethyl acetate. The organic layer was washed with saturated brine and then dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1-[2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(2-trimethylsilanyl-ethoxymethyl)-amino]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-5-yl]-propan-1-ol.

Workup

  1. additionwas added at 0° C.
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1df6e5bdec474d1e80e095e8cd894fa3
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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