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

HRID 129523

反応式

HRID 129523 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.). Analysis for: C20H19NO3Calc'd: C, 74.75; H, 5.96; N, 4.36 Found: C, 74.70; }I, 6.15; N, 4.28

後処理

  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)

出典と根拠

ORDレコード
ord-9a7ac737dda348b9a442606cc9073f1e
出典データセット
uspto-grants-1995_11
特許番号
US05468762

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