Formaldehyde → [4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanol

HRID 606545

Reaktionsgleichung

Reaktionsgleichung von HRID 606545
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1.[CH2:27]=[O:28]>CCCCC.C1COCC1>[Si:20]([O:19][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:27][OH:28])=[CH:8][CH:9]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilaneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 67046104[4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanolAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyllithium (6.6 mL of a 1.7 M solution in pentane, 11.32 mmol) was added to a solution of the aryl bromide 7 (2.0 g, 5.39 mmol) in THF (22 mL) at −78° C. After 0.5 h paraformaldehyde (323 mg, 8.09 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 6:1 hex/EtOAc) yielded 1.2 g (69%) of the alcohol 8 as a clear, colorless oil.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-67fbe19536ed4065ad1c29c3c4d64a78
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915316B2

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