4-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acid → 4-(Adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acid

HRID 1427873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427873
[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH:22]=[CH2:23])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:24])[CH:14]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H][H]>[Pd].C(OCC)(=O)C>[C:1]12([CH2:11][O:12][C:13]3[C:21]([CH2:22][CH3:23])=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[C:15]([F:24])[CH:14]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

5

Edukt 2

HCID 867028964-(Adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acidHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 867028974-(Adamantan-1-ylmethoxy)-5-ethyl-2-fluorobenzoic acidAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-(adamantan-1-ylmethoxy)-2-fluoro-5-vinylbenzoic acid (1.00 g, 3.03 mmol) and 10% palladium on activated carbon (0.10 g) in ethyl acetate (150 mL) was fitted with a hydrogen balloon. The reaction mixture was stirred at ambient temperature for 42 h. The mixture was filtered through a pad of diatomaceous earth, and washed with ethyl acetate (50 mL). The filtrate was concentrated in vacuo, the residue was recrystallized from ethyl acetate and hexanes to afford the title compound as an off-white solid (0.75 g, 74%): 1H NMR (300 MHz, DMSO-d6) δ 12.80 (br s, 1H), 7.63 (d, J=8.6 Hz, 1H), 6.87 (d, J=13.2 Hz, 1H), 3.61 (s, 2H), 5.57 (d, J=7.5 Hz, 2H), 1.99 (s, 3H), 1.75-1.63 (m, 12H), 1.14 (t, J=7.5 Hz, 3H); MS (ES+) m/z 333.2 (M+1).

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washwashed with ethyl acetate (50 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was recrystallized from ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-528aaf4dc5dd47c998af386caa047147
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933236B2

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