Dicyclohexylcarbodiimide → Benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate

HRID 1633

Reaktionsgleichung

Reaktionsgleichung von HRID 1633
[CH2:1]([C:7]1[C:8]([C:21]([OH:23])=[O:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O[C:25]1[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:27][N:26]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([C:7]1[C:8]([C:21]([O:23][C:25]2[CH:40]=[CH:39][C:28]([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])=[CH:27][N:26]=2)=[O:22])=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:17])([CH3:18])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 110125513-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acidHCID 178418417HCID 178418417, Verbindung

Produkt 1

HCID 10973423Benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carboxylic acid were dissolved in 180 ml of methylene chloride. After the addition of a solution of 4.8 g of benzyl 6-hydroxy-nicotinate in 160 ml of methylene chloride and of 2.3 g of 4-dimethylaminopyridine, the solution was cooled to 0° C. and treated with 4.4 g of dicyclohexylcarbodiimide. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours, thereafter poured into ice-cold aqueous ammonium chloride solution, extracted several times with ether, washed with water, dried over sodium sulfate and evaporated. The crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1) and recrystallized from hexane. After repeated crystallization of the mother liquor there were obtained all together 5.7 g of benzyl 6-(3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinate in colorless crystals, m.p. 94°-95° C.

Aufarbeitung

  1. additionpoured into ice-cold aqueous ammonium chloride solution
  2. extractionextracted several times with ether
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. filtrationThe crude product, for the most part crystalline, was filtered over silica gel (eluent hexane/ethyl acetate=9:1)
  7. customrecrystallized from hexane
  8. customcrystallization of the mother liquor

Quellen und Nachweise

ORD-Eintrag
ord-c4710f63ab8144a9acdfc1350b467c98
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726191

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