Diisobutylaluminum hydride → 4-Iodo-2-methoxybenzyl alcohol

HRID 514534

Reaktionsgleichung

Reaktionsgleichung von HRID 514534
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1COCC1>[I:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Komponenten

5

Edukt 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 22619468Benzoic acid, 4-iodo-2-methoxy-, methyl ester

Produkt 1

HCID 187797924-Iodo-2-methoxybenzyl alcoholAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of methyl 4-iodo-2-methoxybenzoate (840 mg, 2.88 mmol) in THF was purged with nitrogen and cooled to −78° C. DIBALH (6 mL, 5.75 mmol, 1M in toluene) was added slowly. The mixture was then stirred at the same temperature for an hour. Saturated aqueous NH4Cl solution was added, followed by extraction with ethyl acetate twice. The organic phase was then washed with brine and dried with anhydrous Na2SO4. Solvent was removed and the resulting residue purified by flash column chromatograph to give 237 mg of the title compound (31%). 1H NMR (400 MHz, CDCl3): δ 2.17 (1H, s), 3.84 (3H, s), 4.62 (2H, d, J=4.0 Hz), 7.01 (1H, d, J=7.6 Hz), 7.18 (1H, s), 7.29 (1H, d, J=8.0 Hz).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate twice
  2. washThe organic phase was then washed with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customSolvent was removed
  5. customthe resulting residue purified by flash column chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-1d531f9b47474f1b86623a248e6a9531
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107916B2

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