Chloromethyl Methyl Ether → HCID 11195344, compound

HRID 1294158Notes

Reaction equation

HRID 1294158 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]1[CH2:18]CC[CH2:15]1.[H-].[Na+].COCCl>O>[CH3:15][O:14][CH2:18][O:13][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][CH:9]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 15555156(2-Phenyl-1,3-oxazol-4-yl)methanol

Product 1

HCID 11195344HCID 11195344, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (2-phenyl-4-oxazolyl)methanol (15.60 g) and tetrahydrofuran (300 mL) was added sodium hydride (60%, oil, 4.28 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Chloromethyl methyl ether (9.34 g) was added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 15 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 4-methoxymethoxymethyl-2-phenyloxazole as a colorless oil (10.86 g, 56%) from a fraction eluted with ethyl acetate-hexane (1:8, v/v).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 15 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e1f78721a4dc48bb8d01953d176a49bc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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