Diisobutylaluminumhydride → {5-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyrazin-2-yl}methanol
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][N:24]=[C:23]([C:26]3[N:27]=[CH:28][C:29]([C:32](OCC)=[O:33])=[N:30][CH:31]=3)[N:22]=2)=[CH:17][CH:16]=1)[CH:12]([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[CH2:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]2[O:25][N:24]=[C:23]([C:26]3[N:27]=[CH:28][C:29]([CH2:32][OH:33])=[N:30][CH:31]=3)[N:22]=2)=[CH:19][CH:20]=1)[CH:12]([CH3:14])[CH3:13]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
Diisobutylaluminum hydride (1.5 M solution in toluene, 2.12 mL) was added dropwise to a cold (−78° C.) solution of ethyl 5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyrazine-2-carboxylate (0.51 g, 1.45 mmol) in toluene (10 mL) and stirred for 0.5 hours at −78° C. The reaction mixture was warmed to 0° C., quenched with 1N HCl (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound (0.50 g) as a crude orange oil.
Workup
- temperatureThe reaction mixture was warmed to 0° C.
- customquenched with 1N HCl (10 mL)
- extractionextracted with EtOAc (3×10 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-7f13977ca89b4e5cb5d52708e2098ecc
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07671043B2
Reaction notes
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