Diethyl Ether → HCID 22722111, compound

HRID 1581653Notes

Reaction equation

HRID 1581653 reaction equation
CON(C)[C:4](=[O:18])[C:5]1[CH:10]=[C:9]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)[CH:8]=[CH:7][C:6]=1[O:16][CH3:17].[CH3:20][Mg]I.CCOCC.[Cl-].[NH4+]>O1CCCC1>[O:15]1[CH2:14][CH2:13][O:12][CH:11]1[C:9]1[CH:8]=[CH:7][C:6]([O:16][CH3:17])=[C:5]([C:4](=[O:18])[CH3:20])[CH:10]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 22722113HCID 22722113, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 22722111HCID 22722111, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-5-(1,3-dioxolan-2-yl)-2-methoxybenzamide (6.60 g, 24.7 mmol) and dehydrated tetrahydrofuran (200 mL) were mixed, and under an atmosphere of argon, the mixture was cooled using dry ice-acetone bath, and 3.0 mol/L solution of methyl magnesium iodide in ether (24.7 mL, 74.1 mmol) was added dropwise slowly under stirring. After completion of the dropwise addition, the mixture was stirred for 1.5 hours under cooling with ice. A saturated aqueous solution of ammonium chloride (200 mL) was added dropwise thereto under cooling with ice and stirring. After separated the organic layer, the aqueous layerwas extracted with ethyl acetate. Respective organic layers were combined, washed with water and saturated brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=4:1 v/v) to obtain 4.31 g (79%) of the title compound as colorless crystals.

Workup

  1. temperatureunder an atmosphere of argon, the mixture was cooled
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred for 1.5 hours
  4. temperatureunder cooling with ice
  5. temperatureunder cooling with ice
  6. stirringstirring
  7. customAfter separated the organic layer
  8. extractionthe aqueous layerwas extracted with ethyl acetate
  9. washwashed with water and saturated brine in sequence
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=4:1 v/v)

Sources & evidence

ORD record
ord-e822b150c68d4b27b3b6c74bd546aef3
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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