Benzyl Bromide → 5-(benzyloxy)-2-methoxytetrahydro-2H-pyran

HRID 520396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520396
[CH3:1][O:2][CH:3]1[O:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.CCOCC>[CH2:13]([O:9][CH:6]1[CH2:7][O:8][CH:3]([O:2][CH3:1])[CH2:4][CH2:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 122006502H-Pyran-3-ol, tetrahydro-6-methoxy-

Produkt 1

HCID 857695615-(benzyloxy)-2-methoxytetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

At 0° C. to a solution of 6-methoxytetrahydro-2H-pyran-3-ol (222 mg, 1.680 mmol) in DMF (2 mL) was added 60% NaH (81 mg, 2.02 mmol) and the mixture was allowed to warm to rt and stirred at rt for 30 min. A solution of (bromomethyl)benzene (345 mg, 2.016 mmol) in DMF (1 ml) was added and the mixture was stirred at rt for 18 h. The reaction mixture was diluted with ether and quenched with water. The crude product was purified by silica gel FCC (20% EtOAc in hexanes) to afford 5-(benzyloxy)-2-methoxytetrahydro-2H-pyran. 1H NMR (400 MHz, CDCl3) δ ppm 7.29-7.41 (5H, m), 4.53-4.64 (3H, m), 3.90 (1H, dd, J=12.05, 2.51 Hz), 3.56-3.65 (1H, m), 3.46-3.53 (1H, m), 3.43 (3H, s), 1.97-2.14 (2H, m), 1.69-1.81 (1H, m), 1.48-1.60 (1H, m).

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 18 h
  2. customquenched with water
  3. customThe crude product was purified by silica gel FCC (20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fc3594e140664113ae855d9f75a89493
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326973B2

Notizen zur Reaktion

Wird geladen…