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

HRID 1816406ノート

反応式

HRID 1816406 の反応式
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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-0012fe911cf944efb5f5fd1d1c66166c
出典データセット
uspto-grants-2005_04
特許番号
US06884814B2

反応ノート

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