Hydrochloric Acid → 1-{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-ethanone

HRID 1734006Notes

Reaction equation

HRID 1734006 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:48]1[CH:49]=[C:50]([C:54](=[O:56])[CH3:55])[CH:51]=[CH:52][CH:53]=1.Cl>C1COCC1.O>[CH3:21][C:20]1[O:19][C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:53]1[CH:52]=[CH:51][C:50]([C:54](=[O:56])[CH3:55])=[CH:49][CH:48]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 84873-HydroxyacetophenoneHCID 11776TriphenylphosphineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 106872271-{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-ethanoneYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Diethylazodicarboxylate (20.7 mL, 131.6 mmol) in THF (35 mL) was added dropwise in to a cold (0° C.) solution of 4-(2'-hydroxy-ethyl)-5-methyl-2-phenyloxazole (25.0 g, 123.0 mmol), triphenylphosphine (34.5 g, 131.6 mmol), and 3'-hydroxyacetophenone (18.0 g, 131.6 mmol) and THF (180 mL). The mixture was allowed to come to room temperature and stirred for 48 hours. Then, it was poured into H2O, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexane/EtOAc 5/1) gave a white solid (30.5 g, 77% yield, m.p. 70°-71° C.).

Workup

  1. customto come to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography on silica gel (hexane/EtOAc 5/1)

Sources & evidence

ORD record
ord-211d8ebe8e614327be25e93c02d54675
Source dataset
uspto-grants-1996_07
Patent number
US05532256

Reaction notes

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