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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 1665959
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1665959
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
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Komponenten

6

Edukt 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

Produkt 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 acidAusbeute 64,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 311Citric AcidLösungsmittel
HCID 887
Methanol
Lösungsmittel
HCID 3939Lithium HydroxideLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2e6e2832073a4bdebacbe46f910f7f47
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08039644B2

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