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 1055178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055178
[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 208,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Glutaric anhydride (115 mg, 1.01 mmol) and retinol (240 mg, 0.838 mmol) were dissolved in dichloromethane (3 mL) in an amber-colored vial. Triethylamine (257 ul, 1.84 mmol) was added and the vial was flushed with argon. Reaction was allowed to stir at room temperature overnight. The reaction mixture was concentrated and then purified via silica gel chromatography with a dichloromethane/methanol gradient to yield 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 as a yellowish oil (700 mg, 78%). Material characterized by NMR.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-39cfbc2a0cc444518d7ea2dbf18601f6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393315B2

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