Sodium Iodide → 2-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl ester

HRID 234229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 234229
[CH2:1]([O:4][C:5](=[O:27])[C:6]1[C:11]([CH:12]=O)=[C:10]([O:14][Si:15]([CH3:23])([CH3:22])[C:16]([CH3:21])([CH3:20])[CH:17]([CH3:19])[CH3:18])[CH:9]=[C:8]([O:24][CH3:25])[C:7]=1[Cl:26])[CH:2]=[CH2:3].[I-:28].[Na+].C[Si](C)(C)Cl.C[SiH2]O[Si](C)(C)C>C(#N)C>[CH2:1]([O:4][C:5](=[O:27])[C:6]1[C:11]([CH2:12][I:28])=[C:10]([O:14][Si:15]([CH3:23])([CH3:22])[C:16]([CH3:21])([CH3:20])[CH:17]([CH3:19])[CH3:18])[CH:9]=[C:8]([O:24][CH3:25])[C:7]=1[Cl:26])[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 529377352-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-formyl-3-methoxy-benzoic acid allyl esterHCID 57376941Tetramethyl disiloxane

Produkt 1

HCID 529377372-Chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl esterAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 3;3 g of 2-chloro-5-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-6-formyl-3-methoxy-benzoic acid allyl ester in 4 ml of acetonitrile were added 1.8 g of sodium iodide and 1.6 ml of trimethyl-chlorosilane. A white precipitate occurred. The mixture was stirred for 5 min at 20° C. The suspension was cooled to 0° C. and 1.48 ml of tetramethyldisiloxane were added. The mixture was stirred for 2 hours at 0° C. and then partitioned between 20 ml of ethyl acetate and 20 ml of water. The aqueous phase was extracted twice with 20 ml of ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was chromatographed on silica gel using diethyl ether/hexane (3:1, v/v) as eluent to afford 3.39 g of 2-chloro-5-[dimethyl-(1,1,2-trimethylpropyl)-silanyloxy]-6-iodomethyl-3-methoxy-benzoic acid allyl ester as a colorless oil.

Aufarbeitung

  1. temperatureThe suspension was cooled to 0° C.
  2. stirringThe mixture was stirred for 2 hours at 0° C.
  3. custompartitioned between 20 ml of ethyl acetate and 20 ml of water
  4. extractionThe aqueous phase was extracted twice with 20 ml of ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5302584099b8472c8da41fd105e6695c
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594135

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