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

HRID 1860059ノート

反応式

HRID 1860059 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-272c04313cbb47389ede0eb8bedb13a2
出典データセット
uspto-grants-2003_03
特許番号
US06528525B1

反応ノート

読み込み中…