Diisobutylaluminum hydride → 4-Iodo-2-methoxybenzyl alcohol

HRID 878690

Reaction equation

HRID 878690 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 187797924-Iodo-2-methoxybenzyl alcoholYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c3c1d2163e084f7c999cef57990de3f3
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Linked notes

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