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Acetone → 2-(1-{5-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile

HRID 1690749
Notes
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Reaction equation

HRID 1690749 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:35][C:36]([CH3:38])=[O:37]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH:16]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[C:36]([OH:37])([CH3:38])[CH3:35])[CH:14]=[N:13][CH:12]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 180AcetoneHCID 2733832Lithium hexamethyldisilazaneHCID 57781102HCID 57781102, compound

Product 1

HCID 577810882-(1-{5-[2-(Tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-{5-[2-(tert-Butyldimethylsilanyloxy)-ethyl]-imidazol-1-ylmethyl}-benzonitrile (1.14 g, 3.34 mmol) is dissolved in THF (20 mL) and cooled to −78° C. LHMDS (1M in THF, 5 mL, 5 mmol) is added dropwise. Ten min after the end of addition, acetone (0.295 g, 5.01 mmol) is added. The reaction mixture is stirred at −78° C. for 40 min. It is then quenched with saturated aqueous sodium bicarbonate (10 mL). The mixture is allowed to warm to room temperature, then poured into water. After extraction with ethyl acetate the organic phase is dried over Na2SO4 and concentrated in vacuo to give 2-(1-{5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-yl}-2-hydroxy-2-methyl-propyl)-benzonitrile; MS (ESI) m/z 400.3 (M+H)

Workup

  1. additionis added
  2. customIt is then quenched with saturated aqueous sodium bicarbonate (10 mL)
  3. temperatureto warm to room temperature
  4. additionpoured into water
  5. extractionAfter extraction with ethyl acetate the organic phase
  6. dry with materialis dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8475d40bbd5f46ce8da91fe6814838c2
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153674B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes