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

HRID 2221571Notes

Reaction equation

HRID 2221571 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][CH:8]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][C:14]=2[O:21][CH3:22])[N:10]=1.S(Cl)([Cl:25])=O>>[Cl:25][CH2:19][C:16]1[CH:17]=[CH:18][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][CH:8]=2)=[C:14]([O:21][CH3:22])[CH:15]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69215267(4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanol

Product 1

HCID 230763434-[(4-Chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazoleYield 74%

Procedure

(4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanol (5.0 g) was added to thionyl chloride (5 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated and ethyl acetate was added to the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-2-(2-furyl)-1,3-oxazole as pale-brown crystals (3.95 g, yield 74%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 123-124° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate was added to the residue
  3. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate, saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-896bb66f1413436bb18ce9d6b95f8610
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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