Thionyl Chloride → HCID 17861276, compound

HRID 349954Notes

Reaction equation

HRID 349954 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 hour. After the reaction mixture was concentrated, saturated aqueous sodium bicarbonate solution was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain 4-(5-chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazole (2.59 g, yield 75%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 129–130° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationAfter the reaction mixture was concentrated
  3. additionsaturated aqueous sodium bicarbonate solution was added to the mixture, which
  4. extractionwas extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e74af304934a484690b8c3813fa0dddf
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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