Diisobutylaluminumhydride → HCID 68595861, compound
Reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH2:19][CH3:20])=[N:8][N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:10]=1[CH2:11][CH3:12])C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:19]([C:7]1[C:6]([CH2:5][CH2:4][OH:3])=[C:10]([CH2:11][CH3:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:8]=1)[CH3:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Dissolve (3,5-diethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-acetic acid ethyl ester (0.54 g, 1.88 mmol) in tetrahydrofuran (20 mL) and cool to −78° C. Add diisobutyl-aluminum hydride (7.52 mL, 7.52 mmol, 1 M in toluene) dropwise and continue to stir for 2.5 hr. Warm to room temperature over 1 hr. then quench with saturated aqueous potassium sodium tartrate solution (50 mL). Add ethyl acetate (100 mL) and stir at room temperature for 16 hr. Separate the organic layer, dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography, eluting with 80:20 hexanes:ethyl acetate, to give 2-(3,5-diethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethanol as a white solid (0.30 g, 66%). 1H-NMR (400 MHz, CDCl3) δ 8.39 (m, 1H), 7.80 (d, 1H), 7.73 (m, 1H), 7.12 (m, 1H), 3.72 (m, 2H), 3.08 (q, 2H), 2.67 (m, 4H), 1.58 (bs, 1H), 1.28 (t, 3H), 1.15 (t, 3H).
Workup
- temperatureWarm to room temperature over 1 hr
- customthen quench with saturated aqueous potassium sodium tartrate solution (50 mL)
- stirringAdd ethyl acetate (100 mL) and stir at room temperature for 16 hr
- customSeparate the organic layer
- dry with materialdry (sodium sulfate)
- filtrationfilter
- concentrationconcentrate
- customPurify
- washeluting with 80:20 hexanes
Sources & evidence
- ORD record
- ord-b18e04058fda421fa16187501390afbc
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202873B2
Reaction notes
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