Thionyl Chloride → HCID 23076545, compound

HRID 2221509Notes

Reaction equation

HRID 2221509 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:21])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH2:19]O)[CH:16]=[CH:17][CH:18]=2)[N:10]=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[Cl:24][CH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][CH2:11][C:9]1[N:10]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[O:7][C:8]=1[CH3:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69217134(3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol

Product 1

HCID 23076545HCID 23076545, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol (8.0 g) and toluene (100 mL) was added thionyl chloride (4.00 g), and the mixture was heated under reflux for 2 hrs. The reaction mixture was concentrated and ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:4, v/v) to give {4-[(3-chloromethylphenoxy)methyl]-2-(2-furyl)-5-methyl-1,3-oxazole as a colorless oil (8.40 g, yield 99%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-36ff81c64d264ccdac2f81b921fa5656
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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