Glutaric anhydride → 5-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanoic acid

HRID 1055176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055176
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[CH2:15][CH2:14][CH2:13][C:12]([CH3:17])([CH3:16])[C:11]=1/[CH:18]=[CH:19]/[C:20](/[CH3:29])=[CH:21]/[CH:22]=[CH:23]/[C:24](/[CH3:28])=[CH:25]/[CH2:26][OH:27].C(N(CC)CC)C>ClCCl>[CH3:28]/[C:24](/[CH:23]=[CH:22]/[CH:21]=[C:20](\[CH3:29])/[CH:19]=[CH:18]/[C:11]1[C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][CH2:15][C:10]=1[CH3:9])=[CH:25]\[CH2:26][O:27][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8]

Komponenten

5

Edukt 3

HCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 445354Retinol

Produkt 1

HCID 866757085-(((2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl)oxy)-5-oxopentanoic acidAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Glutaric anhydride (220 mg, 1.93 mmol) and retinol (500 mg, 1.75 mmol) were dissolved in dichloromethane (5 mL) in an amber-colored vial. Triethylamine (513 ul, 3.68 mmol) was added and the vial was flushed with argon. Reaction mixture was allowed to stir at room temperature for 4 hours. The material was concentrated and purified by silica gel chromatography with a dichloromethane/methanol gradient. Fractions were pooled and concentrated to yield yellowish oil (700 mg). The product was verified by NMR.

Aufarbeitung

  1. customthe vial was flushed with argon
  2. customReaction mixture
  3. concentrationThe material was concentrated
  4. custompurified by silica gel chromatography with a dichloromethane/methanol gradient
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-78dc2e3693d3410abffa35948ae2d156
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393315B2

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