4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 2-(2-Dodecylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 1031637Notes

Reaction equation

HRID 1031637 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CO[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:24][CH2:25][C:26]([CH3:29])([CH3:28])[N:27]=1>O1CCCC1>[CH2:1]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[O:24][CH2:25][C:26]([CH3:29])([CH3:28])[N:27]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 178443215HCID 178443215, compound

Product 1

HCID 140975692-(2-Dodecylphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To freshly prepared dodecylmagnesium bromide (from 30.13 mmoles of dodecyl bromide and 26.20 mmoles of magnesium) in distilled tetrahydrofuran (50 ml) was added 2-(2-methoxyphenyl) 4,4-dimethyloxazoline [A. I. Meyers et al., J. Org. Chem., 43, 1372 (1978)] (17.88 mmoles) in tetrahydrofuran (30 ml). The resultant yellow solution was stirred under argon at ambient temperature for 20 hours. The solution was cooled in an ice water bath and quenched with aqueous ammonium chloride (100 ml). The reaction product was extracted into diethyl ether (100 ml) and the organic phase was washed with saturated sodium chloride solution (50 ml) and then dried over anhydrous magnesium sulfate. Evaporation of the organic phase afforded a colorless oil which was purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant to afford the desired product as a pale yellow oil.

Workup

  1. temperatureThe solution was cooled in an ice water bath
  2. customquenched with aqueous ammonium chloride (100 ml)
  3. extractionThe reaction product was extracted into diethyl ether (100 ml)
  4. washthe organic phase was washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the organic phase
  7. customafforded a colorless oil which
  8. customwas purified by flash chromatography over silica gel with 5 percent ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-e62fbffa06b44e1cb9452b551df821dc
Source dataset
uspto-grants-1990_09
Patent number
US04954513

Reaction notes

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