1-Bromo-3-methylbutane → 2-(Isopentyloxy)-1-naphthaldehyde

HRID 1832334

Reaktionsgleichung

Reaktionsgleichung von HRID 1832334
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13].[H-].[Na+].Br[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>C1COCC1>[CH2:17]([O:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13])[CH2:18][CH:19]([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 78911-Bromo-3-methylbutaneHCID 128192-Hydroxy-1-naphthaldehydeHCID 24758Sodium hydride

Produkt 1

HCID 220486042-(Isopentyloxy)-1-naphthaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Hydroxy-1-naphthaldehyde (1.72 g, 10.0 mmol) and THF (50 ml) were combined in a flask. NaH (312 mg, 13 mmol) was added, followed by 1-bromo-3-methylbutane (1.20 mL, 10.0 mmol). The solution was stirred at room temperature overnight, the solvent was removed in vacuo, and the residue was purified by chromatography (5–10% ethyl acetate/hexane): 1H NMR (400 MHz, CDCl3) δ 10.9 (s, 1H), 9.28 (dd, 1H, J=0.7 Hz, 8.6 Hz), 8.02 (d, 1H, J=9.1 Hz), 7.75 (d, 1H, J=8.1 Hz), 7.63–7.59 (m, 1H), 7.43–7.39 (m, 1H), 7.27 (d, 1H, J=9.2 Hz), 4.25 (t, 2H, J=6.5 Hz), 1.98–1.84 (m, 1H), 1.80–1.75 (m, 2H), 0.99 (d, 6H, J=6.6 Hz); ESMS m/e: 242.8 (M+H)+.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by chromatography (5–10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6252a49c395649d9a42f7573b4201995
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067534B1

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