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Citric Acid → [(3S)-6-({3',5'-dichloro-2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

HRID 416196
ノート
印刷プレビュー

反応式

HRID 416196 の反応式
[Cl:1][C:2]1[C:3]([CH3:40])=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]3[CH:39]=[CH:38][C:29]4[C@H:30]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:31][O:32][C:28]=4[CH:27]=3)[CH:19]=2)[C:5]([CH3:17])=[C:6]([Cl:16])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13].CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:40])=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]3[CH:39]=[CH:38][C:29]4[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=4[CH:27]=3)[CH:19]=2)[C:5]([CH3:17])=[C:6]([Cl:16])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59342584methyl [(3S)-6-({3',5'-dichloro-2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

生成物 1

HCID 24857376[(3S)-6-({3',5'-dichloro-2',6'-dimethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid
収率 86%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of methyl [(3S)-6-({3′,5′-dichloro-2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate (0.617 g, 1.02 mmol) in a mixed solvent of methanol (2 mL) and tetrahydrofuran (4 mL) was added 2 M aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was diluted with water, acidified with 10% aqueous citric acid solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals were recrystallized from heptane-ethyl acetate to give the title compound (0.520 g, yield 86%) as colorless crystals.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe precipitated crystals were recrystallized from heptane-ethyl acetate

出典と根拠

ORDレコード
ord-63f1929556904c239db068a021d07010
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08088821B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート