Lithium hydroxide, monohydrate → ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 603404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603404
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[C@H:21]([CH2:25][C:26]([O:28]CC)=[O:27])[CH2:20][CH2:19]4)=[CH:10][C:5]=2[O:4][CH:3]=1.O[Li].O>C1COCC1.O>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[C@H:21]([CH2:25][C:26]([OH:28])=[O:27])[CH2:20][CH2:19]4)=[CH:10][C:5]=2[O:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59300536ethyl ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate

Produkt 1

HCID 24776386((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetic acidAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of ethyl ((1S)-5-{3-[(3-methyl-1-benzofuran-6-yl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (119 mg, 0.29 mmol) (Example 64) in THF (4.2 mL) was added a solution of LiOH.H2O (15 mg, 0.35 mmol) in water (1.4 mL). The mixture was stirred for 4 h at 45° C. and then 12 h at rt. The reaction mixture was concentrated under reduced pressure, water was added, and the aqueous phase was washed with a small volume of Et2O. The pH was adjusted to below 3 with HCl (1 N aqueous solution), and the aqueous phase was extracted with excess EtOAc. The combined EtOAc extracts were dried, filtered, and concentrated under reduced pressure to give 24 mg (22%) of the title compound as a solid. 1H NMR (300 MHz, CDCl3): δ 7.44-7.22 (m, 2H), 7.08 (d, 1H), 6.98 (s, 1H), 6.89 (d, 1H), 6.80 (s, 1H), 6.72 (d, 1H), 4.32-4.04 (m, 4H), 3.63-3.44 (m, 1H), 2.98-2.76 (m, 3H), 2.58-2.37 (m, 2H), 2.37-2.14 (m, 5H), 1.88-1.70 (m, 1H); LC-MS: RT=3.53 min, (M+H)+ 381.1.

Aufarbeitung

  1. custom12 h
  2. customat rt
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. washthe aqueous phase was washed with a small volume of Et2O
  6. extractionthe aqueous phase was extracted with excess EtOAc
  7. dry with materialThe combined EtOAc extracts were dried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7e01d6d592e14bf18711b75cd1ba6d94
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906653B2

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