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m-Chloroperbenzoic acid → Di-tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutyl phosphate

HRID 2238327
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238327
[Si:1]([O:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.C(N(CC)[P:24]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])C.ClC1C=CC=C(C(OO)=[O:45])C=1>ClCCl.C(Cl)(Cl)Cl>[P:24]([O:13][CH2:12][C:11]([CH3:15])([CH3:14])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:45]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 70297m-Chloroperbenzoic acid2×HCID 4251849Di-tert-butyl diethylphosphoramiditeHCID 197346474-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-olHCID 178418441HCID 178418441, Verbindung

Produkt 1

HCID 86616510Di-tert-butyl 4-{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutyl phosphateAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-45 °C

Versuchsvorschrift

To a solution of the product from Example 10A (0.630 g, 2.7 mmol) and 1H-tetrazole (0.568 g) in dichloromethane (11.0 mL) at room temperature was added di-t-butyl diethylphosphoramidite (1.02 g), and the solution was allowed to stir for 1 hour. The solution was cooled to −45° C., followed by addition of m-chloroperbenzoic acid (1.33 g). After 1 hour at −45° C., additional m-chloroperbenzoic acid (1.33 g) was added and the mixture was allowed to warm to room temperature and was stirred for 16 hours. The reaction mixture was diluted with chloroform and washed with 10% Na2CO3 and brine, and was dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with 20% ethyl acetate in hexane, to give the title compound (0.441 g, 38%).

Aufarbeitung

  1. waitAfter 1 hour at −45° C.
  2. temperatureto warm to room temperature
  3. stirringwas stirred for 16 hours
  4. washwashed with 10% Na2CO3 and brine
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-94ef3185c8b34e4fa6ebfd1514a91471
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718633B2

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