Reaktion #1060530

ord-a4a6ee54287f4478a7a4a27be83a958c

Reaktionsgleichung

CCCCC[C@@H](CCCC(CCCCCCC(=O)OCC)(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OC1CCCCO1
Di-tert.-butyl 2-[4(S)-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate
C1CCOC1
tetrahydrofuran
Cl
hydrochloric acid
→
CCCCC[C@H](O)CCCC(CCCCCCC(=O)OCC)(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
title compound
CCCCC[C@H](O)CCCC(CCCCCCC(=O)OCC)(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C
Di-tert.-butyl 2-[4-(S)-hydroxynonyl]-2-(6-ethoxycarbonylhexyl)malonate

Edukte

CCCCC[C@@H](CCCC(CCCCCCC(=O)OCC)(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)OC1CCCCO1
Di-tert.-butyl 2-[4(S)-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate
C1CCOC1
tetrahydrofuran
Cl
hydrochloric acid

Reagenzien

Keine

Lösungsmittel

O
water
CCOCC
ether

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with four portions of water
  2. 2
    Trocknenwith brine and dried over sodium sulfate
  3. 3
    workup.DISTILLATIONDistillation of the ether in vacuo

Vorschrift

Di-tert.-butyl 2-[4(S)-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate (47.8 g., 0.08 mole) is added to a mixture of tetrahydrofuran (300 ml.) and 6N hydrochloric acid (15 ml.). The resulting solution is allowed to stand at room temperature for 6 hours. The solution is then diluted with 1.5 liters of water. The oily product is taken up in ether, washed with four portions of water, and with brine and dried over sodium sulfate. Distillation of the ether in vacuo leaves the title compound as a residual oil weighing 39.5 g.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04055597uspto-grants-1977_10