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Hydrogen Peroxide → HCID 23372103, Verbindung

HRID 1900286
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1900286
[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]([CH3:23])([CH3:22])[CH2:6]1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:33].[Na+].OO>O1CCCC1.O.CCOCC>[CH2:14]([O:13][N:8]1[C:7]([CH3:22])([CH3:23])[CH2:6][CH:5]([O:4][CH2:1][CH2:2][CH2:3][OH:33])[CH2:10][C:9]1([CH3:11])[CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 233721064-Allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 23372103HCID 23372103, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 14.9 grams (45.9 mmol) of 4-allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 10A) in 20 ml of anhydrous tetrahydrofuran is added over a 10-minute period to a solution of 5.6 grams (45.9 mmol ) of 9-borabicyclo [3.3.1]nonane in 20 ml of tetrahydrofuran under a nitrogen atmosphere. The reaction mixture is cooled to 20° C., and a solution of 1.84 gram ( 45.9 mmol ) of sodium hydroxide in water is added over a 10-minute period. A solution of 15.3 ml of 30% aqueous hydrogen peroxide is then added over 30 minutes while the reaction mixture is cooled in an ice-water bath. The reaction mixture is diluted with ether (50 ml) and the organic layer is separated and dried over potassium carbonate. Solvent is evaporated and the residue is purified by flash chromatography (silica gel; 2:1 heptane:ethyl acetate) to afford 14.0 grams (89% yield) of the title compound is a colorless syrup.

Aufarbeitung

  1. temperatureis cooled in an ice-water bath
  2. customthe organic layer is separated
  3. dry with materialdried over potassium carbonate
  4. customSolvent is evaporated
  5. customthe residue is purified by flash chromatography (silica gel; 2:1 heptane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-706b7a64ecf94061b62dd72b09fb4a64
Quelldatensatz
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05574162

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