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Acetic Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

HRID 1822343
ノート
印刷プレビュー

反応式

HRID 1822343 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2].C(O)(=O)C.[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[CH3:22])=[CH:9][C:8]=1[CH3:23])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 690715883-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 578941493-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester収率 85.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 702
Ethanol
溶媒

実験手順

A solution of 3-[4-(5-methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester (1.18 g, 3.63 mmol) and palladium under carbon (10%) (0.39 g, 0.36 mmol) in ethanol (20 mL) and acetic acid (2 mL) is stirred under 1 atm of hydrogen. After stirring overnight, the mixture is filtered off through Celite and washed with methanol. The mixture is concentrated under reduced pressure and purified by flash chromatography by eluting with hexane:ethyl acetate 5:1 to afford the title compound (1.02 g, 85%). Rf=0.42 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.26 (t, 3H, J=6.9 Hz), 2.16 (s, 3H), 2.28 (s, 3H), 2.56 (t, 2H, J=7.3 Hz), 2.90 (t, 2H, J=7.3 Hz), 3.72 (s, 3H), 4.17 (q, 2H, J=6.9 Hz), 6.45 (d, 1H, J=2.4 Hz), 6.62 (dd, 1H, J=2.8, 8.5 Hz), 6.67 (dd, 1H, J=2.4, 8.1 Hz), 6.74 (d, 1H, J=2.4 Hz), 7.06 (d, 1H, J=8.1 Hz), 7.13 (d, 1H, J=8.1 Hz).

後処理

  1. filtrationthe mixture is filtered off through Celite
  2. washwashed with methanol
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by flash chromatography
  5. washby eluting with hexane:ethyl acetate 5:1

出典と根拠

ORDレコード
ord-6ab7d7faceac4d55a972c9fae23f7c2b
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07608639B2

反応ノート

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