Toluene → HCID 23076344, compound

HRID 2221547Notes

Reaction equation

HRID 2221547 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9]([CH2:11][O:12][C:13]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][C:14]=2[C:15]([O:17][CH3:18])=[O:16])[N:10]=1.C1(C)C=CC=CC=1.S(Cl)([Cl:35])=O>C(OCC)(=O)C>[Cl:35][CH2:23][C:20]1[CH:21]=[CH:22][C:13]([O:12][CH2:11][C:9]2[N:10]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[O:7][C:8]=2[CH3:25])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 23076465HCID 23076465, compound

Product 1

HCID 23076344HCID 23076344, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-5-hydroxymethylbenzoate (2.50 g) and toluene (100 mL) was added thionyl chloride (0.95 g), and the mixture was heated under reflux for 1 hr. After concentration of the reaction mixture, ethyl acetate was added to the residue, and the mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated to give methyl 5-chloromethyl-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate as colorless crystals (2.23 g, yield 84%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 107-108° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. washthe mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-37860cfbcf174f63acb39de9702dcffc
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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