Boron trifluoride etherate → Cyclododecanecarboxaldehyde

HRID 129531

Reaktionsgleichung

Reaktionsgleichung von HRID 129531
[O:1]1[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.CCCCCC.CCCCCC.C(OCC)(=O)C>CCOCC>[CH:3]1([CH:2]=[O:1])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Komponenten

6

Edukt 4

HCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 110198001-Oxaspiro[2.11]tetradecaneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 78737CyclododecanecarboxaldehydeAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 5.0 g (25.5 mmol) of 1-oxaspiro[2.11]tetradecane in 50 ml of dry ether at 0° C. is slowly added 1.8 ml (2.1 g, 14.6 mmol) of boron trifluoride etherate. The ice bath is removed and after 15 minutes at room temperature the solution is partitioned between ether and saturated sodium bicarbonate. The organic phase is evaporated to give a clear oil. Flash chromatography over silica gel using a hexane to hexane:ethyl acetate (9:1) gradient give 1.6 g (34%) of a clear oil: NMR (CDCl3) δ 1.28-1.8 (m, 18 H), 2.03 (s, 1 H), 2.42 (m, 1 H), 9.62 (s, 1 H)

Aufarbeitung

  1. customat 0° C.
  2. customThe ice bath is removed and after 15 minutes at room temperature the solution
  3. customis partitioned between ether and saturated sodium bicarbonate
  4. customThe organic phase is evaporated
  5. customto give a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-05973ff767bc42be89cf6d7b85a7564c
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468774

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