Hydrochloric Acid → 1-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid

HRID 881076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 881076
C[O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]3[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[C:12]=3[CH:18]=2)[CH2:7][CH2:6]1)=[O:4].[Li+].[OH-].Cl>CO>[CH3:16][C:13]1([CH3:17])[C:12]2[CH:18]=[C:8]([C:5]3([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]3)[CH:9]=[CH:10][C:11]=2[O:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 591293551-(3,3-Dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester

Produkt 1

HCID 591295061-(3,3-Dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acidAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 1-(3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-cyclopropanecarboxylic acid methyl ester (1 g, 4 mmol) in MeOH (10 mL) was added LiOH (0.40 g, 9.5 mmol). The mixture was stirred at 40° C. overnight. HCl (10%) was added slowly to adjust the pH to 5. The resulting mixture was extracted with ethyl acetate (10 mL×3). The extracts were washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the crude product was purified by preparative HPLC to give 1-(3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid (0.37 g, 41%). 1H NMR (400 MHz, CDCl3) δ 7.11-7.07 (m, 2 H), 6.71 (d, J=8 Hz, 1 H), 4.23 (s, 2 H), 1.66-1.63 (m, 2 H), 1.32 (s, 6 H), 1.26-1.23 (m, 2 H).

Aufarbeitung

  1. extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
  2. washThe extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9e9fea9f33174329a4150336fc738d7e
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993600B2

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