4-Toluenesulfonyl chloride → HCID 86661967, Verbindung

HRID 1959962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1959962
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:18]=[CH:17][C:12]([O:13][CH2:14][CH2:15][OH:16])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33](C)=[CH:32][CH:31]=1)(=[O:29])=[O:28]>CN(C)C1C=CN=CC=1.ClCCl>[C:30]1([S:27]([O:16][CH2:15][CH2:14][O:13][C:12]2[CH:17]=[CH:18][C:9]([B:4]3[O:3][C:2]([CH3:19])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)(=[O:29])=[O:28])[CH:36]=[CH:35][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 231341922-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-ol

Produkt 1

HCID 86661967HCID 86661967, VerbindungAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into dichloromethane 100 ml, 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethanol (4.4 g, 16.7 mmol) synthesized in Example 2 (2b) was dissolved, to which triethylamine (4.6 ml, 33.2 mmol), 4-dimethylaminopyridine (400 mg, 3.3 mmol), tosyl chloride (4.8 g, 25.2 mmol) were sequentially added while cooling with ice. The resulting mixture was warmed back to room temperature, followed by further stirring for two hours. The resulting reaction liquid was sequentially washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V) to give the desired title compound (6.1 g, yield 88%).

Aufarbeitung

  1. additionwere sequentially added
  2. temperaturewhile cooling with ice
  3. customThe resulting reaction liquid
  4. washwas sequentially washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-b582397e7e804f28b374c4c8992f6f0e
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410273B2

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