P-Cresol → Ethyl 3-(4-benzyloxyphenyl)-2-(4-methylphenoxy)propionate

HRID 1860059노트

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HRID 1860059 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:28]S(C)(=O)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:33]1[C:38](O)=[CH:37][CH:36]=[C:35]([CH3:40])[CH:34]=1>CN(C)C=O>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([O:28][C:38]2[CH:37]=[CH:36][C:35]([CH3:40])=[CH:34][CH:33]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 2879P-CresolHCID 11430Potassium CarbonateHCID 18625936Ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate

생성물 1

HCID 18625971Ethyl 3-(4-benzyloxyphenyl)-2-(4-methylphenoxy)propionate수율 27.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

Potassium carbonate (8.09 g) was added to a solution of ethyl 3-(4-benzyloxyphenyl)-2-methanesulfonyloxypropionate (11.1 g), which is the product of Reference example 35(a), and p-cresol (2.85 g) in N,N-dimethylformamide (110 ml). This mixture was stirred at 70° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel column using hexane/ethyl acetate=9/1 as the eluant to afford the desired compound (2.84 g) as a colorless oil.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified via chromatography on silica gel column

출처 및 근거

ORD 기록
ord-272c04313cbb47389ede0eb8bedb13a2
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528525B1

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