2-(2,3-Dimethoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole → HCID 10243704, compound

HRID 1250086Notes

Reaction equation

HRID 1250086 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].CO[C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[C:16]1[O:17][CH2:18][C:19]([CH3:22])([CH3:21])[N:20]=1>O1CCCC1>[CH:1]([C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[C:16]1[O:17][CH2:18][C:19]([CH3:21])([CH3:22])[N:20]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 111282672-(2,3-Dimethoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 10243704HCID 10243704, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Isopropylmagnesium chloride (2.0M in diethyl ether) (18.75 ml, 37.5 mmol) was added dropwise to a solution of 2-(2,3-dimethoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (7.06 g, 30.0 mmol) in freshly distilled tetrahydrofuran at room temperature. The mixture was stirred overnight, quenched with water, and diluted with diethyl ether. The layers were separated, and the aqueous layer was washed twice with diethyl ether. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel flash chromatography, eluting with hexane/ethyl acetate, gave 2-(2-isopropyl-3-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole as a clear oil (7.08 g, 95.4%).

Workup

  1. customquenched with water
  2. additiondiluted with diethyl ether
  3. customThe layers were separated
  4. washthe aqueous layer was washed twice with diethyl ether
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel flash chromatography
  8. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-0cef4f51848a418d98be06d115324207
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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