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Methyl morpholine oxide → Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

HRID 1921879
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1921879
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:32])[C:20]=1[O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH2:5][CH:6]([CH2:16][OH:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:32][C:19]1[CH:18]=[C:4]([CH2:5][CH:6]([CH:16]=[O:17])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:2]([F:1])[C:20]=1[O:21][Si:22]([CH:26]([CH3:27])[CH3:28])([CH:29]([CH3:31])[CH3:30])[CH:23]([CH3:24])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 82029Methyl morpholine oxideHCID 57971930Ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate

Produkt 1

HCID 57971915Ethyl 7-(3,5-difluoro-4-triisopropylsilanyloxyphenyl)-6-formylheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419074HCID 178419074, VerbindungKatalysatorHCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

1.19 g (2.52 mmol) of ethyl 6-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-7-hydroxyheptanoate are stirred with 5 g of 4 Å molecular sieves and 442 mg (3.78 mmol) of N-methylmorpholine N-oxide in 50 ml of dichloromethane at room temperature for 10 minutes. 44 mg (0.13 mmol) of tetrapropylammonium perruthenate are added, and the mixture is stirred at room temperature until reaction is complete. The mixture is filtered and the filtrate is washed with water and saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated. The resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). 1.0 g (84% of theory) of the title compound is obtained.

Aufarbeitung

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with water and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-109de2df71b5486db9d65eb79205615a
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08173704B2

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