Triethylamine → 2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone

HRID 77324

Reaktionsgleichung

Reaktionsgleichung von HRID 77324
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1>[C:21]([Si:18]([CH3:20])([CH3:19])[O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4])([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 68490alpha-Hydroxyacetophenone

Produkt 1

HCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanoneAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a well stirred solution of 2-hydroxyacetophenone (1.0 g, 7.34 mmol) in dichloromethane (15 mL) is added triethylamine (1.23 mL, 8.81 mmol), 4-dimethylaminopyridine (45 mg, 0.367 mmol) and tert-butyldimethylsilyl chloride (1.16 g, 7.71 mmol) dissolved in dichloromethane (2 mL). The reaction mixture is stirred at room temperature for 1 h, then diluted with dichloromethane (50 mL), washed with 10% citric acid, saturate sodium carbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (20% ethyl acetate in hexanes) to yield the title compound as a yellow oil (1.3 g, 5.19 mmol).

Aufarbeitung

  1. washwashed with 10% citric acid
  2. concentrationsaturate sodium carbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via silica gel chromatography (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bc682cb8ff3148aa8529b9d5ab9e350a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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