Acetic Anhydride → 3-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-ol

HRID 1816406노트

반응식

HRID 1816406 반응식
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[N:10][OH:11].C(OC(=O)C)(=O)C.CCN(CC)CC.O.[Cl-].[Na+].O>>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=3[O:11][N:10]=2)=[CH:2][CH:7]=1

참가 물질

5

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23713072Sodium chloride dihydrateHCID 136342142(2,4-Dihydroxyphenyl)(4-hydroxyphenyl)methanone Oxime

생성물 1

HCID 1355269583-(4-Hydroxy-phenyl)-benzo[d]isoxazol-6-ol수율 44.7%

실험 절차

A mixture of (2,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone oxime (0.46 g, 1.87 mmol), acetic anhydride (0.19 g, 1.87 mmol) and Et3N (0.25 g, 2.44 mmol) was stirred at room temperature for 24 h. The mixture was pored into water/brine and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05) gave an off-white solid (0.19 g, 42% yield, m.p. 192-194° C.); MS m/e 226 (M−H)+.

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (CH2Cl2/hexanes/EtOAc/MeOH 5/3.5/1/0.05)

출처 및 근거

ORD 기록
ord-0012fe911cf944efb5f5fd1d1c66166c
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884814B2

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