Ethyl Acetate → 4-(3-Chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

HRID 1295216Notes

Reaction equation

HRID 1295216 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])[CH:11]=1)[CH2:7]O)[CH3:2].S(Cl)([Cl:28])=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:28][CH2:7][C:6]1[CH:9]=[C:10]([CH:11]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[O:12][CH2:13][C:14]1[N:15]=[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:17][C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 694273333-Ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

Product 1

HCID 229306794-(3-Chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazoleYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-ethoxy-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (4.38 g) in toluene (80 ml) was added dropwise thionyl chloride (1.69 g) at room temperature. After stirring for 90 min, ethyl acetate (100 ml) was added to the reaction mixture and the mixture was washed with aqueous sodium bicarbonate and then with water. The organic layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the crystals obtained from the fraction eluted with ethyl acetate-hexane (1:4, volume ratio) were recrystallized from ethyl acetate-hexane to give 4-(3-chloromethyl-5-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole (4.25 g, 92%) as colorless prism crystals. melting point: 86–87° C.

Workup

  1. washthe mixture was washed with aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe crystals obtained from the fraction
  5. washeluted with ethyl acetate-hexane (1:4, volume ratio)
  6. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-24e6ff999b2f448fa86a8917b7447581
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

Loading…