Thionyl Chloride → 4-(5-Chloromethyl-2-methoxyphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazole

HRID 2221514Notes

Reaction equation

HRID 2221514 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH2:21]O)[CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[N:10]=1.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[Cl:26][CH2:21][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([CH:14]=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[CH3:23]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 69217094(3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanol

Product 1

HCID 230764304-(5-Chloromethyl-2-methoxyphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazoleYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanol (7.0 g) and toluene (150 mL) was added thionyl chloride (3.16 g), and the mixture was heated under reflux for 1 hr. 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 to give 4-(5-chloromethyl-2-methoxyphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazole as pale-brown crystals (7.30 g, yield 99%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  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

Sources & evidence

ORD record
ord-a0db373c39e04ffa91259e0deb7d4270
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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