(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol → 4-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde

HRID 238625

Reaktionsgleichung

Reaktionsgleichung von HRID 238625
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=[C:11]([CH2:20][OH:21])[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=[C:11]([CH:20]=[O:21])[C:10]=1[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 59326595(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 593265294-Benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehydeAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (180 mg, 0.6 mmol) in dichloromethane (10 mL) was added pyridinium chlorochromate (260 mg, 1.2 mmol) in portions. After being stirred at room temperature for 3 hours, the resulting dark mixture was diluted with diethyl ether, and stirred at room temperature for 10 minutes. The mixture was filtered through a short silica gel column. The filtrate was concentrated in vacuo to give 4-benzyloxy-6-fluoro-3-methyl-naphthalene-2-carbaldehyde (165 mg, 93%) as a white solid, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 10.31 (s, 1H), 8.16 (s, 1H), 8.00 (dd, J=8.84, 5.56 Hz, 1H), 7.73 (dd, J=10.48, 2.40 Hz, 1H), 7.55 (d, J=6.82 Hz, 2H), 7.39-7.49 (m, 2H), 7.32 (td, J=8.65, 2.65 Hz, 1H), 4.99 (s, 2H), 2.75 (s, 3H).

Aufarbeitung

  1. stirringstirred at room temperature for 10 minutes
  2. filtrationThe mixture was filtered through a short silica gel column
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cf2c744260664e2b98f4d6338dcc58f4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642629B2

Verknüpfte Notizen

Wird geladen…