Chlorotrimethylsilane → 5-Chloro-2-methoxybenzeneethanamine

HRID 494431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494431
Cl[Si](C)(C)C.[BH4-].[Li+].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH2:17][C:18]#[N:19]>O1CCCC1.CO>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[C:11]([CH2:17][CH2:18][NH2:19])[CH:12]=1

Komponenten

6

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 4148881Lithium borohydrideHCID 7131175(5-Chloro-2-methoxyphenyl)acetonitrile

Produkt 1

HCID 209848495-Chloro-2-methoxybenzeneethanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Chlorotrimethylsilane (2 mL, 16 mmol) was added dropwise to lithium borohydride (2M in tetrahydrofuran, 4 mL, 8 mmol). A solution of 2-methoxy-5-chlorophenylacetonitrile (312 mg, 4 mmol) in tetrahydrofuran (2 mL) was then added at 0° C. and the mixture was allowed to stir for 24 hours, whilst warming to room temperature. The mixture was then diluted with methanol (20 mL) and concentrated in vacuo. The residue was taken up in 20% potassium hydroxide solution (20 mL), extracted with dichloromethane (3×20 mL) and the combined organic solution was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography using an Isolute® SCX-2 cartridge, eluting with methanol followed by 1M ammonia in methanol, to give an oily residue. The oil was triturated with diethyl ether to afford the title compound, 485 mg.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionextracted with dichloromethane (3×20 mL)
  3. dry with materialthe combined organic solution was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with methanol
  7. customto give an oily residue
  8. customThe oil was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-26291ecccac0476f955a0636b0864d6e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538141B2

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