Tetrahydrofuran → 3-((tert-Butyldimethylsilyl)oxy)-4-methoxybenzaldehyde

HRID 1028922

Reaktionsgleichung

Reaktionsgleichung von HRID 1028922
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(N(C(C)C)CC)(C)C.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O1CCCC1>CN(C)C=O.C(Cl)(Cl)Cl.O>[Si:21]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 12127IsovanillinHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Produkt 1

HCID 3595583-((tert-Butyldimethylsilyl)oxy)-4-methoxybenzaldehydeAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a cooled solution of 3-hydroxy-4-methoxybenzaldehyde 12 (10.0 g, 65.7 mmol) in dry N,N-dimethyl formamide (75 mL) was added diisopropylethylamine (16.99 g, 131.4 mmol). Before the addition of 1.0 M solution of tert-butyldimethylsilyl chloride in tetrahydrofuran (11.89 g or 78.9 mL, 78.85 mmol) the mixture was stirred under nitrogen for 10 min. After complete addition over 30 min, the reaction mixture was left overnight (12-16 h). Reaction completion was checked by TLC (chloroform on silica gel plate). Water was added to the reaction mixture, extracted with dichloromethane and the organic layer was washed with a saturated sodium bicarbonate solution, water and dried. Removal of solvent in vacuo yielded as an oil which was subjected to column chromatography (eluant: chloroform) to afford as an yellow viscous oil 13 (100%). 1H NMR: δ 0.21 (s, 6H, 2×CH3), 1.01 (s, 9H, 3×CH3), 3.91 (s, 3H, OCH3), 6.94 (d, 1H, J=8.5 Hz, 5H), 7.36 (d, 1H, J=2 Hz, 2H), 7.47 (dd, 1H, J=8.5, 2 Hz, 6H), 9.89 (s, 1H, CHO). Anal. Calcd for C14H22O3Si: C, 63.12, H, 8.32. Found: C, 63.09, H, 8.30.

Aufarbeitung

  1. additionAfter complete addition over 30 min
  2. waitthe reaction mixture was left overnight (12-16 h)
  3. customReaction completion
  4. extractionextracted with dichloromethane
  5. washthe organic layer was washed with a saturated sodium bicarbonate solution, water
  6. customdried
  7. customRemoval of solvent in vacuo
  8. customyielded as an oil which

Quellen und Nachweise

ORD-Eintrag
ord-b175faa0fdb742aca3a8a4144a4129e2
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735620B2

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