Diisobutylaluminumhydride → (3-Amino-5-ethoxy-4-iodo-phenyl)-methanol

HRID 502368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502368
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]([I:13])=[C:6]([NH2:14])[CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[NH2:14][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]=1[I:13]

Komponenten

4

Edukt 2

HCID 21225700DiisobutylaluminumhydrideHCID 684595793-Amino-5-ethoxy-4-iodo-benzoic acid methyl ester

Produkt 1

HCID 68454929(3-Amino-5-ethoxy-4-iodo-phenyl)-methanolAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-5-ethoxy-4-iodo-benzoic acid methyl ester (0.18 g, 0.56 mmol) in THF (5 mL) at 0° C. under Ar was slowly added diisobutylaluminium hydride (2.8 mL, 2.80 mmol, 1 M solution in THF) over a time period of 30 min, the cooling bath removed on completion of addition and the reaction allowed to reach rt. After 2 h, the excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL). The solidified mixture was extracted with hot THF, the combined organic phases concentrated by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1) providing 0.056 g (34%) of the title compound.

Aufarbeitung

  1. customat 0° C.
  2. customover a time period of 30 min
  3. customthe cooling bath removed on completion of addition
  4. customto reach rt
  5. customthe excess hydride was quenched by cautious addition of a sat. solution of potassium sodium tartrate (50 mL)
  6. extractionThe solidified mixture was extracted with hot THF
  7. concentrationthe combined organic phases concentrated by evaporation under reduced pressure
  8. customthe crude material purified with column chromatography on silica eluting with hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-1dd62d4f5a7d46f0acb6c13f4404ed69
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

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