Pyridine → 4-(3-Methyl-5-phenyl-pentyloxycarbonyloxy)-undecanoic acid 2-naphthalen-2-yl-2-oxo-ethyl ester

HRID 1384415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384415
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[O:27])[CH2:12][O:13][C:14](=[O:26])[CH2:15][CH2:16][CH:17]([OH:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].N1C=CC=CC=1.[CH3:34][CH:35]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:36][CH2:37][OH:38].Cl[C:48]([O-])=[O:49]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[O:27])[CH2:12][O:13][C:14](=[O:26])[CH2:15][CH2:16][CH:17]([O:25][C:48]([O:38][CH2:37][CH2:36][CH:35]([CH3:34])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:49])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 211868244-Hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl esterHCID 867571413-Methyl-5-phenyl-pentanol chloroformate

Produkt 1

HCID 541043384-(3-Methyl-5-phenyl-pentyloxycarbonyloxy)-undecanoic acid 2-naphthalen-2-yl-2-oxo-ethyl esterAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4.00 g of 4-hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl ester and 1.71 g of pyridine in 20 ml of THF, a solution of 2.91 g of 3-methyl-5-phenyl-pentanol-chloroformate in 10 ml of THF was dropped in at 0° C. The mixture was stirred for 3 hours at room temperature. Then, the reaction mixture was quenched with water and extracted with ether. The organic phase was washed with 2N HCl, saturated sodium bicarbonate, and water. Then, the mixture was dried, filtered, and evaporated to dryness. The resulting yellow oil was purified by chromatography to yield 5.46 g of a colorless oil.

Aufarbeitung

  1. customThen, the reaction mixture was quenched with water
  2. extractionextracted with ether
  3. washThe organic phase was washed with 2N HCl, saturated sodium bicarbonate, and water
  4. customThen, the mixture was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting yellow oil was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d7e18d01bfdf4e978b73d821399304bc
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258854B1

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