Diisobutylaluminum hydride → HCID 59678323, compound

HRID 251616Notes

Reaction equation

HRID 251616 reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:20]([C:24]2[CH:25]=[N:26][C:27]([C:33]3[C:38]([CH2:39][CH3:40])=[CH:37][CH:36]=[CH:35][C:34]=3[CH2:41][CH3:42])=[CH:28][C:29]=2[O:30][CH2:31][CH3:32])[CH2:21][CH2:22][CH3:23])[CH:14]=1>C1COCC1.CCOCC>[CH2:41]([C:34]1[CH:35]=[CH:36][CH:37]=[C:38]([CH2:39][CH3:40])[C:33]=1[C:27]1[N:26]=[CH:25][C:24]([CH:20]([O:19][C:15]2[CH:14]=[C:13]([CH2:12][OH:11])[CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH3:23])=[C:29]([O:30][CH2:31][CH3:32])[CH:28]=1)[CH3:42]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66993668HCID 66993668, compound

Product 1

HCID 59678323HCID 59678323, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1.5 M in Toluene, 0.3 mL) is added dropwise to a solution of 3-{1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butoxy}-benzoic acid methyl ester (80 mg, 0.17 mmol) in THF (3 mL) at room temperature. The reaction mixture is stirred for 2 hours, then diluted with ether (5 mL) and treated with Na2SO4.10H2O. The resulting mixture is stirred for one hour and filtered through Celite. Concentration of the filtrate at reduced pressure gives (3-{1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butoxy}-phenyl)-methanol. 1H NMR (CDCl3) 8.53 (s, 1H), 7.10-7.30 (m, 4H), 6.74-6.90 (m, 4H), 5.60 (m, 1H), 4.51 (s, 2H), 4.13 (, 21), 2.47 (s, 1H), 2.24-2.37 (m, 4H), 1.80-2.10 (m, 2H), 1.4-1.6 (m, 1H), 0.90-1.05 (m, 9H).

Workup

  1. stirringThe resulting mixture is stirred for one hour
  2. filtrationfiltered through Celite

Sources & evidence

ORD record
ord-9fd26c9908b34bf7b8c450ed571af13d
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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