Lithium Hydroxide → HCID 67488047, Verbindung

HRID 1755148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755148
C[O:2][C:3](=[O:33])[CH:4]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.CO.O>[CH2:16]([O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH:4]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:27][CH:28]=2)[C:3]([OH:33])=[O:2])=[CH:7][CH:8]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67486802HCID 67486802, Verbindung

Produkt 1

HCID 67488047HCID 67488047, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To the crude 3-[4-(2-Benzyloxyethoxy)-phenyl]-2-(4-tert-butylphenyl)-propionic acid methyl ester from step d dissolved in 20 mL of THF/MeOH/H2O (3:1:1) was added lithium hydroxide (270 mg, 6.5 mmol) After stirring for 5 hrs at rt, the organic solvents were removed under vacuum and the reaction residue diluted further with water (25 mL). The aqueous mixture was extracted with diethyl ether, made acidic with 1 N HCl and extracted again with ethyl acetate. The ethyl acetate portion was then dried over Na2SO4 and concentrated under vacuum to afford 3-[4-(2-Benzyloxyethoxy)-phenyl]-2-(4-tert-butylphenyl)-propionic acid as a semi-solid mass. (456 mg, 81% over 2 steps)

Aufarbeitung

  1. customthe organic solvents were removed under vacuum
  2. additionthe reaction residue diluted further with water (25 mL)
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. extractionextracted again with ethyl acetate
  5. dry with materialThe ethyl acetate portion was then dried over Na2SO4
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d8fab3215bd0416ca4c71b277ff68dce
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169201B2

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