Thionyl Chloride → HCID 17861276, compound

HRID 1294223Notes

Reaction equation

HRID 1294223 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18].S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[Cl:27][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:5]=1)[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 17861351HCID 17861351, compound

Product 1

HCID 17861276HCID 17861276, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxy-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (3.22 g), thionyl chloride (0.73 ml) and toluene (50 ml) was refluxed for 1 hr. The reaction mixture was concentrated and saturated aqueous sodium hydrogencarbonate was added. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 4-(5-chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazole (2.59 g, yield 75%) as colorless crystals from a fraction eluted with ethyl acetate. The crystals were recrystallized from ethyl acetate-hexane. melting point: 129-130° C.

Workup

  1. temperaturewas refluxed for 1 hr
  2. concentrationThe reaction mixture was concentrated
  3. additionsaturated aqueous sodium hydrogencarbonate was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e8d37bcadd40454783f91c64ff2d0173
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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