Diisobutylaluminum hydride → HCID 59678323, compound

HRID 1392647Notes

Reaction equation

HRID 1392647 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 (q, 2H), 2.47 (s, 1H), 2.24-2.37 (m, 4H), 1.80-2.10 (m, 2H), 1.40-1.60 (m, 5H), 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-252fff8571384abba1f9337746e38d77
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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