Dichloromethane → 1-(tert-Butyldimethylsilyloxy)-2-propanone

HRID 709904

Reaktionsgleichung

Reaktionsgleichung von HRID 709904
C(Cl)Cl.[OH:4][CH2:5][C:6](=[O:8])[CH3:7].CCN(CC)CC.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C1C=CN=CC=1)C.O>[Si:20]([O:4][CH2:5][C:6](=[O:8])[CH3:7])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8299HydroxyacetoneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanoneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a DCM (5 mL) solution of 1-hydroxypropan-2-one (500 mg, 6.8 mmol), DMAP (41 mg, 0.34 mmol) and Et3N (1.2 mL, 8.16 mmol) was added TBSCl (1.133 g, 7.5 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. Then the mixture was added water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (10/1) to give the title compound (950 mg, 75%). EDI-MS (M+1): 189. 1H NMR (300 MHz, CDCl3) δ 4.057 (s, 2H), 2.080 (s, 3H), 0.832 (s, 9H), 0.001 (s, 6H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6e48db2831a6490e90b4fc5c64604832
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181191B2

Verknüpfte Notizen

Wird geladen…