Diisobutylaluminum hydride → HCID 11131640, compound

HRID 1170974Notes

Reaction equation

HRID 1170974 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:24])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)[C:5](OC)=[O:6].CC(C[AlH]CC(C)C)C>C1COCC1>[CH:21]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][CH3:20])[O:12][C:11]1[C:10]([Cl:24])=[CH:9][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[Cl:1])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 10904699HCID 10904699, compound

Product 1

HCID 11131640HCID 11131640, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3,5-dichloro-4-(3′-iso-propyl-4′-methoxyphenoxy)-benzoate (1.40 g, 3.37 mmol) in THF (10.0 mL) at 0° C. was added a solution of DIBAL-H (8.12 μL, 8.12 mmol, 1.0 M solution in THF). 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 MgSO4, filtered and concentrated under reduced pressure to afford 4-(3′-iso-propyl-4′-methoxyphenoxy)-3,5-dichlorobenzyl alcohol as an off-white solid (0.94 g, 100%): 1H NMR (300 MHz, DMSO-d6): δ 7.54 (s, 2 H), 6.81 (m, 2 H), 6.40 (m, 1 H), 5.51 (m, 1 H), 4.54 (d, J=6.0 Hz, 2 H), 3.75 (s, 3 H), 3.21 (m, 1 H), 1.13 (d, J=6.0 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (17:3); 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 MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6c0276f79ba45f79ac75bdc77c8d4d8
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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