Ethyl Acetate → (R,R,R)-2-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,6-dimethyl-3-propyl-[1,4]benzoquinone

HRID 63813

Reaktionsgleichung

Reaktionsgleichung von HRID 63813
[CH2:1]([C:4]1[C:5](=[O:34])[C:6]([CH3:33])=[C:7]([CH3:32])[C:8](=[O:31])[C:9]=1[CH2:10][CH2:11][C@@:12]([OH:30])([CH3:29])[CH2:13][CH2:14][CH2:15][C@H:16]([CH3:28])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:2]=[CH2:3].CCOC(C)=O>C(Cl)Cl.O=[Pt]=O>[OH:30][C@:12]([CH3:29])([CH2:13][CH2:14][CH2:15][C@H:16]([CH3:28])[CH2:17][CH2:18][CH2:19][C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11][CH2:10][C:9]1[C:8](=[O:31])[C:7]([CH3:32])=[C:6]([CH3:33])[C:5](=[O:34])[C:4]=1[CH2:1][CH2:2][CH3:3]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 58771193(R,R,R)-2-allyl-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,6-dimethyl-[1,4]benzoquinone

Produkt 1

HCID 58771181(R,R,R)-2-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,6-dimethyl-3-propyl-[1,4]benzoquinoneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R,R,R)-2-allyl-3-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,6-dimethyl-[1,4]benzoquinone (Ex-1D-4) (50 mg, 0.1 mmol) was hydrogenated using PtO2 (5 mg) at 50 psi for 2 h in a solution of EtOAc (5 mL). The suspension was filtered through celite, which was rinsed with DCM (2×2 mL). The pale yellow solution was concentrated by rotary evaporation to yield a pale yellow oil (Ex-1D-5). The oil was dissolved in DCM (5 mL) and stirred with silica (˜20 mg) for 5 days. The bright yellow suspension was filtered through a cotton plug and concentrated by rotary evaporation to yield (R,R,R)-2-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-5,6-dimethyl-3-propyl-[1,4]benzoquinone (Ex-1D-6) as a bright yellow oil (38 mg, 76%). 1H NMR (400 MHz, CDCl3) δ (ppm): 2.57-2.52 (m, 2H), 2.48-2.44 (m, 2H), 2.02 (s, 6H), 1.57-1.04 (m, 26H), 0.99 (t, J=7.4 Hz, 3H), 0.89-0.85 (m, 15H).

Aufarbeitung

  1. customfor 2 h
  2. filtrationThe suspension was filtered through celite, which
  3. washwas rinsed with DCM (2×2 mL)
  4. concentrationThe pale yellow solution was concentrated by rotary evaporation
  5. customto yield a pale yellow oil (Ex-1D-5)
  6. filtrationThe bright yellow suspension was filtered through a cotton plug
  7. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ba0eea87965e41d3b978b40384f8ea48
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447006B2

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