Thionyl Chloride → 4-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 584398Notes

Reaction equation

HRID 584398 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]O>C1(C)C=CC=CC=1>[Cl:3][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:10][C:6]=1[CH3:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10957398HCID 10957398, compound

Product 1

HCID 110990364-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (1.69 g) was added dropwise to a stirred suspension of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (4.00 g) in toluene (60 ml) at 0° C. After stirring at room temperature for 2 hours, the reaction mixture was concentrated. The residual crystals were dissolved in ethyl acetate and washed with aqueous sodium bicarbonate and water. The ethyl acetate layer was separated, dried (MgSO4), and concentrated to give 4-(2-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole as crystals. Recrystallization from ethyl acetate-hexane gave colorless needles (3.50 g, yield 82%). m.p. 103-104° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residual crystals were dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate and water
  4. customThe ethyl acetate layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-502814b56117410c89185514ad771a42
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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