Triethylamine → 3-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

HRID 456498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456498
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[OH:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[Cl:1])[CH:6]=[O:7])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 138651144-Chloro-3-hydroxybenzaldehyde

Produkt 1

HCID 865980253-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473 ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were concentrated under reduced pressure to give an oil which was purified using SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate:cyclohexane) to give the title compound (0.42 g) as an oil. *Kelley, J; Linn, J; Selway, J. W. T., J. Med. Chem. (1989), 32(8), 1757–63.

Aufarbeitung

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with diethyl ether
  3. concentrationThe combined organic extracts were concentrated under reduced pressure
  4. customto give an oil which
  5. customwas purified
  6. washSPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate:cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-5554586d10fe4c5a8792d3db4b4fa4e5
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186717B2

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