Acetonitrile → HCID 70663854, compound

HRID 476212Notes

Reaction equation

HRID 476212 reaction equation
[C:1](#[N:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+].[C:21]([O:24][CH2:25][CH3:26])(=O)C>>[OH:14][C:18]1[CH:17]=[CH:16][C:15](/[CH:17]=[CH:16]/[C:15](=[O:14])[CH2:2][C:1]#[N:3])=[CH:26][C:25]=1[O:24][CH3:21]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 70663854HCID 70663854, compoundYield 58%

Procedure

Trans-ethyl(4-hydroxy-3-methoxy)cinnamate (222 mg, 1 mmol, manufactured by Fluka), acetonitrile (156 μL, 3 mmol), 1M lithium bis(trimethylsilyl)amide (3 mL, 3 mmol) and tetrahydrofuran (3 mL) were stirred at room temperature for 30 minutes. A saturated ammonium chloride aqueous solution (15 mL) and ethyl acetate (10 mL) were added thereto, followed by separation of layers into two layers and washing with distilled water and saline. The organic layer was dried over anhydrous sodium sulfate and separated by column chromatography (n-Hex/EtOAc=3/1 (v/v)) to afford Compound 10.

Workup

  1. customfollowed by separation of layers into two layers
  2. washwashing with distilled water and saline
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customseparated by column chromatography (n-Hex/EtOAc=3/1 (v/v))

Sources & evidence

ORD record
ord-def80eab22d84ae3b1182e9a8121fea6
Source dataset
uspto-grants-2014_01
Patent number
US08637674B2

Reaction notes

Loading…