Diisobutylaluminum hydride → HCID 67041539, compound

HRID 2108674Notes

Reaction equation

HRID 2108674 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:26])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=1)[C:5](OC)=[O:6].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:26])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:24])[CH3:25])[CH:14]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 25150125HCID 25150125, compound

Product 1

HCID 67041539HCID 67041539, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxybenzyl)benzoate (1.00 g, 2.81 mmol) in THF (11.3 mL) at 0° C. was added a solution of DIBAL-H (8.44 mL, 8.44 mmol, 1.0 M solution in hexanes). The reaction mixture was stirred at room temperature for 16 h, quenched with cold 1 N HCl and diluted with ethyl acetate. The organic layer was washed with 1 N HCl and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford 3,5-dimethyl-4-(3′-iso-propyl-4′-methoxymethoxy-benzyl)benzyl alcohol as an off-white solid (0.75 g, 81.3%): 1H NMR (300 MHz, DMSO-d6): δ 7.54 (s, 2H), 6.81 (m, 2H), 6.40 (m, 1H), 5.51 (m, 1H), 4.54 (d, J=6.0 Hz, 2H), 3.75 (s, 3H), 3.21 (m, 1H), 1.13 (d, J=6.0 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (15:85); Rf=0.27.

Workup

  1. customquenched with cold 1 N HCl
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with 1 N HCl and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa5d515fc56341668a78f29bf9a27584
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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