Hydrochloric Acid → HCID 67110075, compound

HRID 2381241Notes

Reaction equation

HRID 2381241 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]([C:21]#[N:22])=[C:13]([CH:20]=1)[C:14](N(OC)C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Cl-].[NH4+].Cl>C(OCC)(=O)C.O1CCCC1>[C:14]([C:13]1[CH:20]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([O:23][CH3:24])=[CH:11][C:12]=1[C:21]#[N:22])(=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 58345562HCID 58345562, compoundHCID 178418255HCID 178418255, compound3×

Product 1

HCID 67110075HCID 67110075, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-benzyloxy-2-cyano-4,N-dimethoxy-N-methylbenzamide (reference example 6-2) (203 mg) and tetrahydrofuran (3.1 mL) was added phenylmagnesium bromide (1.08 mol/L tetrahydrofuran solution, 0.7 mL) under ice-bath cooling. The mixture was stirred for 1.5 hours. Phenylmagnesium bromide (1.08 mol/L tetrahydrofuran solution, 0.3 mL) was added to the mixture. After stirring under ice-bath cooling for 50 minutes, the mixture was stirred at room temperature overnight. Phenylmagnesium bromide (1.08 mol/L tetrahydrofuran solution, 0.35 mL) was added to the mixture. After stirring at 0° C. for 1.5 hours, to the mixture were added a saturated aqueous solution of ammonium chloride, 1 mol/L hydrochloric acid and ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, water and brine successively, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 0%-30% ethyl acetate/hexane, gradient elution) to give the title compound (112 mg).

Workup

  1. temperaturecooling
  2. stirringAfter stirring under ice-bath
  3. temperaturecooling for 50 minutes
  4. stirringthe mixture was stirred at room temperature overnight
  5. stirringAfter stirring at 0° C. for 1.5 hours, to the mixture
  6. washThe organic layer was washed with 1 mol/L hydrochloric acid, water and brine successively
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: 0%-30% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-d95734e419dd4e64a902db21a258dd94
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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