Acetone → HCID 57781131, compound

HRID 1690753Notes

Reaction equation

HRID 1690753 reaction equation
[N:1]1([CH2:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH:5]=[CH:4][N:3]=[CH:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:25][C:26]([CH3:28])=[O:27].C(=O)(O)[O-].[Na+]>C1COCC1.O>[OH:27][C:26]([CH3:28])([CH3:25])[CH:6]([C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 142311482-(1H-Imidazol-1-ylmethyl)benzonitrile

Product 1

HCID 57781131HCID 57781131, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

2-Imidazol-1-ylmethyl-benzonitrile (1.0 g, 5.49 mmol) is dissolved in THF (10 mL) and cooled to −75° C. LHMDS (1M in THF, 8.24 mL, 8.24 mmol) is added dropwise. Ten min after the end of addition, acetone (0.48 g, 8.24 mmol) is added. Thirty min after the end of addition, saturated aqueous sodium bicarbonate (10 mL) is added and the mixture is allowed to warm to r.t., then poured into water. After extraction with ethyl acetate the organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is used in the next step without further purification; MS (ESI) m/z 242.1 (M+H).

Workup

  1. additionis added
  2. additionis added
  3. temperatureto warm to r.t.
  4. extractionAfter extraction with ethyl acetate the organic phase
  5. dry with materialis dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is used in the next step without further purification

Sources & evidence

ORD record
ord-b5eaab70ab3e49cd8e3f274626d7c061
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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