Hydrochloric Acid → 4-(2-Methyl-1,3-dioxolan-2-yl)benzaldehyde

HRID 497207

Reaktionsgleichung

Reaktionsgleichung von HRID 497207
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH:19](N1CCCCC1)=[O:20].Cl>C1COCC1>[CH:19]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1)=[O:20]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 178418339Butyllithium

Produkt 1

HCID 119615844-(2-Methyl-1,3-dioxolan-2-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 2-(4-bromophenyl)-2-methyl-1,3-dioxolane (2.0 g, 8.23 mmol) in THF (7 ml) was added n-BuLi (1.61 M solution in hexane, 5.47 ml, 8.8 mmol) at −78° C. under nitrogen, and the mixture was stirred for 2 hour, then allowed to warm up to 0° C. for 30 min. A solution of 1-formylpiperidine (930 mg, 8.23 mmol) in THF (5 ml) was added, and the mixture was stirred for 2 hours. The mixture was made neutral by addition of 1N HCl solution, and the whole was extracted with diethylether. The organic layer was washed with saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo. The compound was used for next reaction without purification.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hours
  2. extractionthe whole was extracted with diethylether
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe compound was used for next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-327ab84d4587430891d651c9838efa5f
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949536B2

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