Diethyl Ether → 3-(Oxan-4-yl)propanal

HRID 253578

Reaktionsgleichung

Reaktionsgleichung von HRID 253578
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH:9]=[O:10])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 222728913-(Oxan-4-yl)propan-1-ol

Produkt 1

HCID 574496833-(Oxan-4-yl)propanalAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(tetrahydro-pyran-4-yl)-propan-1-ol (11.8 g, 0.0825 mol) in CH2Cl2 (200 mL) was added Dess-Martin periodinane (70.27 g, 0.165 mol). The mixture was stirred at rt. When the reaction was complete, the solution was poured into Et2O (300 mL) and anhydrous K2CO3 (19.84 g, 0.165 mol) was added. The mixture was filtered. The filtrate was dried over Na2SO4, and concentrated under vacuum to give the crude product, which was purified by column chromatography to give 3-(tetrahydro-pyran-4-yl)-propionaldehyde (8.59 g, 83%). 1H NMR (CD3OD) δ 1.1-1.3 (m, 4H), 1.4-1.6 (m, 5H), 2.4-2.5 (t, 2H), 3.2-3.3 (m, 2H), 3.8-3.97 (m, 2H), 9.7-9.8 (s, 1H).

Aufarbeitung

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. dry with materialThe filtrate was dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto give the crude product, which
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ba07b43497c5406a8a380f9c2ec9510d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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