Dichloromethane → 4-Tert-butyldimethylsilyloxymethyl-2-allylphenol

HRID 257821

Reaktionsgleichung

Reaktionsgleichung von HRID 257821
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)C=C.C(N([CH2:18][CH3:19])CC)C.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[CH2:28](Cl)Cl>C(OCC)(=O)C>[Si:20]([O:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[C:12]([CH2:28][CH:18]=[CH2:19])[CH:11]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Komponenten

6

Edukt 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanol

Produkt 1

HCID 199348384-Tert-butyldimethylsilyloxymethyl-2-allylphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the product of Step A (650 mg, 3.96 mmol) in CH2Cl2 (20 mL), cooled to 0° C. under nitrogen, was added triethylamine (612 mL, 4.39 mmol) and a solution of tert-butyldimethylsilyl chloride (631 mg; 4.19 mmol) in CH2Cl2 (2 mL). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (60 mL), washed with water, and saturated sodium bicarbonate, and then dried (MgSO4). The filtrate was concentrated in vacuo to afford 1.1 g of the title compound which was used crude in the next reaction (Rf =0.45, 5% ethyl acetate/hexanes).

Aufarbeitung

  1. washwashed with water, and saturated sodium bicarbonate
  2. dry with materialdried (MgSO4)
  3. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d8d2590ded8469297d4eab6f0d4da32
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264439

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