Cyclohexanemethanol → Cyclohexanemethanol

HRID 63325

Reaktionsgleichung

Reaktionsgleichung von HRID 63325
[CH:1]1([CH2:7][O:8][C:9]2[O:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:16]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl.O=[Mn]=O>[CH:1]1([CH2:7][O:8][C:9]2[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:16]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 2

HCID 7507CyclohexanemethanolHCID 86694621(5-(Cyclohexylmethoxy)furan-2-yl)methanol

Produkt 2

HCID 7507CyclohexanemethanolHCID 866946205-(Cyclohexylmethoxy)furan-2-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (5-(cyclohexylmethoxy)furan-2-yl)methanol and cyclohexylmethanol (0.75 g) and MnO2 (3.16 g, 36.3 mmol) in anhydrous CH2Cl2 (16 mL) was stirred at room temperature for 3 days. The reaction mixture was filtered through Celite and concentrated under reduced pressure. Flash chromatography purification (10%-50% EtOAc—hexanes gradient) gave 5-(cyclohexylmethoxy)furan-2-carbaldehyde with cyclohexylmethanol as an impurity as a light yellow. Yield (0.68 g, 99%); 1H NMR (400 MHz, DMSO-d6) δ 9.20 (s, 1H), 7.52 (d, J=3.8 Hz, 1H), 5.79 (d, J=3.8 Hz, 1H), 4.03 (d, J=5.8 Hz, 2H), 1.55-1.80 (m, 6H), 0.96-1.25 (m, 5H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customFlash chromatography purification (10%-50% EtOAc—hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-bbdce7758206446ab1203684ebfbdd2e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447078B2

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