Acetonitrile → 4-Methoxybenzoylacetonitrile

HRID 1695205Notes

Reaction equation

HRID 1695205 reaction equation
[C:1]([O:11]C)(=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:23](#[N:25])[CH3:24]>>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([C:1](=[O:11])[CH2:24][C:23]#[N:25])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 8499Methyl anisateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 2333984-MethoxybenzoylacetonitrileYield 73%

Procedure

A solution of methyl p-anisate in acetonitrile was cooled to −10° C. Lithium bis(trimethylsilyl)amide (1 M in THF) was added dropwise over a minimum of 3 hr. The mixture was held at −10 to 0° C. until reaction completion. The reaction mixture was quenched with water and the pH adjusted to 3-4 with conc HCl. The mixture was stirred for 1 hr. The product was isolated by filtration, washed with water and dried in a vacuum oven. The yield was 73%.

Workup

  1. customThe mixture was held at −10 to 0° C. until reaction completion
  2. customThe reaction mixture was quenched with water
  3. customThe product was isolated by filtration
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-00e3b1a4ecc54ef9a18ff89fec0c5871
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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