Diisobutylaluminum hydride → 467235-07-0
Reaction equation
CON(C)[C:4]([C:6]1[CH:17]=[CH:16][C:9]2[N:10]=[N:11][N:12]([CH:13]([CH3:15])[CH3:14])[C:8]=2[CH:7]=1)=[O:5].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH:13]([N:12]1[C:8]2[CH:7]=[C:6]([CH:4]=[O:5])[CH:17]=[CH:16][C:9]=2[N:10]=[N:11]1)([CH3:15])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred, cold (−78° C.) solution of 3-isopropyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide (4.26 g) in 20 mL of toluene was added drop-wise 17.2 mL of DIBAL in toluene (1 M). The mixture was stirred for 1 hour at −78° C. before warming to 0° C. The reaction was quenched with aqueous 1 N hydrochloric acid, diluted with water and extracted with ethyl acetate (3 times). The combined extracts were washed with water, brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to give a yellow oil. This oil was purified by flash chromatography (eluting with 2:1 hexanes/ethyl acetate) to give 2.24 g of 3-isopropyl-3H-benzotriazole-5-carbaldehyde as a yellow oil which crystallized upon standing; MS 190 M+1.
Workup
- temperaturebefore warming to 0° C
- customThe reaction was quenched with aqueous 1 N hydrochloric acid
- additiondiluted with water
- extractionextracted with ethyl acetate (3 times)
- washThe combined extracts were washed with water, brine
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customto give a yellow oil
- customThis oil was purified by flash chromatography (eluting with 2:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-e433f6f7a72945a8848cfff19cef3189
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664395B2
Reaction notes
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