Tetrahydrofuran → HCID 23025010, compound

HRID 349956Notes

Reaction equation

HRID 349956 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[N:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:21][C:22]=1[CH3:23])[CH2:11]O)[CH3:6].O1CCCC1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:3][CH2:11][C:10]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[C:8]([O:7][CH2:5][CH3:6])[CH:9]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 69423214HCID 69423214, compound

Product 1

HCID 23025010HCID 23025010, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (0.73 ml) was added slowly to a mixture of 3-ethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (3.05 g), tetrahydrofuran (25 ml) and toluene (50 ml) at room temperature, which was stirred at 80° C. for 30 minutes. After cooling, the reaction mixture was poured into an aqueous saturated sodium bicarbonate solution, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate solution, dried (MgSO4) and concentrated to obtain 4-(4-chloromethyl-2-ethoxyphenoxymethyl)-5-methyl-2-phenyloxazole (2.94 g, yield 91%) as colorless crystals. This was recrystallized from tetrahydrofuran-hexane. Melting point: 138–139° C.

Workup

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf54786395764c019a522e5529fb5597
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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