Water → HCID 10496538, compound

HRID 1957765Notes

Reaction equation

HRID 1957765 reaction equation
CO[C:3]1[C:8](OC)=[C:7]([C:11]2[O:12][CH2:13][C:14]([CH3:17])([CH3:16])[N:15]=2)[CH:6]=[CH:5][C:4]=1[C:18]1[O:19][CH2:20][C:21]([CH3:24])([CH3:23])[N:22]=1.[CH2:25]([Mg]Br)[CH3:26].[Cl-].[NH4+].O.O1CC[CH2:34][CH2:33]1>>[CH2:33]([C:8]1[C:3]([CH2:25][CH3:26])=[C:4]([C:18]2[O:19][CH2:20][C:21]([CH3:23])([CH3:24])[N:22]=2)[CH:5]=[CH:6][C:7]=1[C:11]1[O:12][CH2:13][C:14]([CH3:16])([CH3:17])[N:15]=1)[CH3:34]

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 10735330HCID 10735330, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 10496538HCID 10496538, compoundYield 100%

Procedure

In 20 mL of anhydrous tetrahydrofuran, was dissolved 2.00 g (6.02 mmol) of 2,2'-(2,3-dimethoxy-1,4-phenylene)-bis(4,4-dimethyl-2-oxazoline). Thereto, 16.4 mL of 0.92M ethylmagnesium bromide solution (15.1 mmol) in tetrahydrofuran was added dropwise with ice cooling in 30 minutes, and the mixture was stirred at room temperature for 2 hours. To the reaction liquid, were added successively 10 mL of aqueous saturated ammonium chloride solution and 30 mL of water. The product was extracted from the mixture with ether, washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to obtain 1.98 g (100%) of 2,2'-(2,3-diethyl-1,4-phenylene)-bis(4,4-dimethyl-2-oxazoline) in a colorless prism crystal state.

Workup

  1. customTo the reaction liquid
  2. extractionThe product was extracted from the mixture with ether
  3. washwashed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-cf199668c659453a89f35eb3fe9ed741
Source dataset
uspto-grants-1998_07
Patent number
US05786486

Reaction notes

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