Acetaminophen → Methyl 4-(4-acetamidophenoxy)benzoate

HRID 23374

反応式

HRID 23374 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:19]2[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 1983AcetaminophenHCID 27343694-Methoxycarbonylphenylboronic acid

生成物 1

HCID 22573305Methyl 4-(4-acetamidophenoxy)benzoate収率 75.1%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

Dry air is bubbled through a solution of 4-acetamidophenol (320 mg, 2.1 mmol), copper(II) acetate (384 mg, 2.1 mmol), TEA (1.5 mL, 10.5 mol), (4-methoxycarbonylphenyl)boronic acid (760 mg, 4.2 mmol), and powdered molecular sieves (2 g) in CH2Cl2 (21 mL) for 16 hours at room temperature. The resulting material is concentrated and purified by flash column chromatography (25-50% EtOAc in heptane) to give methyl 4-(4-acetamidophenoxy)benzoate (450 mg, 75%). 1H NMR (300 MHz, DMSO) δ 8.01, 7.54, 7.27, 7.05, 6.98, 3.92, 2.22.

後処理

  1. customDry air
  2. customfor 16 hours
  3. customat room temperature
  4. concentrationThe resulting material is concentrated
  5. custompurified by flash column chromatography (25-50% EtOAc in heptane)

出典と根拠

ORDレコード
ord-6135df3391b94ab680a5652fa0de43f5
出典データセット
uspto-grants-2005_02
特許番号
US06852716B2

関連ノート

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