Hydrogen Peroxide → 3-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-ol

HRID 2206775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206775
[CH2:1]([C:4]1[C:17]([Br:18])=[CH:16][C:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:14]([Cl:28])[C:5]=1[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH:2]=[CH2:3].CSC.B.[OH-:33].[Na+].OO>C1COCC1.O>[Br:18][C:17]1[C:4]([CH2:1][CH2:2][CH2:3][OH:33])=[C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9])[C:14]([Cl:28])=[C:15]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:16]=1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86714082(2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane

Produkt 1

HCID 867140833-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-olAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of bromide 186 (2.57 g, 5.33 mmol) in THF (35 mL) was added borane dimethylsulfide complex (10M in THF, 0.18 mL, 1.76 mmol) at 0° C. The mixture was stirred at rt for 1 hr. The mixture was cooled to 0° C. and H2O (0.5 mL), aq. 3N NaOH solution (1.1 mL), 35% H2O2 (0.65 mL) were added to the mixture.) The mixture was stirred at 50° C. for 30 min and cooled to rt. The mixture was extracted with EtOAc/aq. 50% NaCl solution (100 mL/100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 187 (1.73 g, 65%).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. stirring) The mixture was stirred at 50° C. for 30 min
  3. temperaturecooled to rt
  4. extractionThe mixture was extracted with EtOAc/aq
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b9737884513241aa88b1e102ef006154
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371303B2

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