Tetrahydrofuran → HCID 59389357, compound

HRID 2357952Notes

Reaction equation

HRID 2357952 reaction equation
COCN[C:5]([C:7]1[C:8]2[N:9]([N:15]=[C:16]([CH2:18][CH3:19])[CH:17]=2)[C:10](OC)=[CH:11][CH:12]=1)=[O:6].[CH2:20]([Mg]Br)[CH3:21].[Cl-].[NH4+].O1CC[CH2:28][CH2:27]1>>[CH2:18]([C:16]1[CH:17]=[C:8]2[C:7]([C:5](=[O:6])[CH2:20][CH3:21])=[CH:12][CH:11]=[C:10]([CH2:27][CH3:28])[N:9]2[N:15]=1)[CH3:19]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 68461169HCID 68461169, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 59389357HCID 59389357, compound

Procedure

The compound of Example 349 (11.09 g) was dissolved in tetrahydrofuran (320 mL) in an argon atmosphere. While this solution was chilled in a ice salt water bath (−7° C.), ethyl magnesium bromide (100 mL, 0.91 mol/L tetrahydrofuran solution) was added dropwise and the mixture was stirred at room temperature for 1 hour. Subsequently, a saturated aqueous ammonium chloride solution was added while the mixture was chilled in an ice bath. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel chromatography (hexane:ethyl acetate=2:3→1:2→1:4→ethyl acetate) afforded the title compound as a yellow powder (4.21 g).

Workup

  1. additionwas added dropwise
  2. temperaturewas chilled in an ice bath
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the solvent and subsequent purification of the residue by silica gel chromatography (hexane:ethyl acetate=2:3→1:2→1:4→ethyl acetate)

Sources & evidence

ORD record
ord-8c4055e8beab451fb1c968cafa2ea465
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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