Acetaminophen → Methyl 4-(4-acetamidophenoxy)benzoate

HRID 23374

반응식

HRID 23374 반응식
[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]

참가 물질

5

반응물 2

HCID 1983AcetaminophenHCID 27343694-Methoxycarbonylphenylboronic acid

생성물 1

HCID 22573305Methyl 4-(4-acetamidophenoxy)benzoate수율 75.1%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6135df3391b94ab680a5652fa0de43f5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852716B2

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