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3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester → 3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid

HRID 2240820
ノート
印刷プレビュー

反応式

HRID 2240820 の反応式
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([C:29]([F:32])([F:31])[F:30])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:33][CH3:34])C>C1COCC1.CO.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:28][C:25]1([CH3:27])[CH2:24][CH2:23][C:22]2=[C:18]([C:16](=[O:17])[CH2:15][CH2:14][C:10]3[CH:11]=[C:12]([CH3:13])[C:7]([CH2:6][CH2:5][C:4]([OH:35])=[O:3])=[C:8]([CH2:33][CH3:34])[CH:9]=3)[S:19][C:20]([C:29]([F:32])([F:30])[F:31])=[C:21]2[CH2:26]1
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 1

HCID 575089143-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester

生成物 1

HCID 167354333-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid収率 64.2%

試薬・触媒・溶媒 4

HCID 311Citric Acid溶媒HCID 887Methanol溶媒
HCID 3939
Lithium Hydroxide
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester (340 mg, 0.668 mmol) in THF (5 mL), methanol (4 mL) and 2 N aq. LiOH (2 mL) is stirred at rt for 2 h before it is diluted with 10% aq. citric acid solution and extracted with DCM (3×75 mL). The combined organic extracts are dried over MgSO4, filtered and the solvent of the filtrate is evaporated. The crude product is purified on prep. TLC plates with heptane:EA 3:4 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid (206 mg) as a colourless glass; LC-MS: tR=1.17 min, [M+1]=481.36.

後処理

  1. extractionextracted with DCM (3×75 mL)
  2. dry with materialThe combined organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent of the filtrate is evaporated
  5. customThe crude product is purified on prep

出典と根拠

ORDレコード
ord-f22d479d39d84d69b58c49100ad4f434
出典データセット
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07723378B2

反応ノート

読み込み中…

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