Sodium Iodide → HCID 58771180, Verbindung

HRID 63817

Reaktionsgleichung

Reaktionsgleichung von HRID 63817
[CH3:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH2:6][CH2:7][C@:8]([CH2:14][CH2:15][CH2:16][C@@H:17]([CH2:19][CH2:20][CH2:21][C@@H:22]([CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH3:23])[CH3:18])([CH3:13])[O:9]2)=[CH:4][C:3]=1[OH:30].C([O-])([O-])=O.[K+].[K+].Cl[CH2:38][C:39]([CH3:41])=[CH2:40].[Na+].[I-]>O.C(Cl)Cl.CCOC(C)=O.CC(C)=O>[CH3:13][C@@:8]1([CH2:14][CH2:15][CH2:16][C@H:17]([CH3:18])[CH2:19][CH2:20][CH2:21][C@H:22]([CH3:23])[CH2:24][CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:7][CH2:6][C:5]2[C:10](=[C:11]([CH3:12])[C:2]([CH3:1])=[C:3]([O:30][CH2:40][C:39]([CH3:41])=[CH2:38])[CH:4]=2)[O:9]1

Komponenten

9

Edukt 4

HCID 5238Sodium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 92729(+)-gamma-Tocopherol

Produkt 1

HCID 58771180HCID 58771180, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(+)-γ-tocopherol (Ex-1F-1) (300 mg, 0.72 mmol), K2CO3 (199 mg, 1.44 mmol), 3-chloro-2-methyl propene (450 μL, 5.17 mmol), NaI (˜10 mg) and acetone (8 mL) were charged to a 50 mL RBF. The reaction was heated to reflux for 20 h after which time it was deemed complete by TLC (1:9 EtOAc:Hept). The reaction was diluted with water (15 mL) and DCM (10 mL). The aqueous layer was separated and washed with DCM (3×10 mL). The combined DCM layers were dried over Na2SO4, filtered and concentrated by rotary evaporation to yield (R,R,R)-2,7,8-trimethyl-6-(2-methyl-allyloxy)-2-(4,8,12-trimethyl-tridecyl)-chroman as a pale yellow liquid (Ex-1F-2) (324 mg, 95%). The isolated product was used without any further purification.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 20 h after which time it
  3. customThe aqueous layer was separated
  4. washwashed with DCM (3×10 mL)
  5. dry with materialThe combined DCM layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9dffcebc806947d8aa9c5258463d726a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447006B2

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