Allyl Alcohol → [3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[N:9][OH:10])=[N:6][CH:7]=1.[CH2:11]([OH:14])[CH:12]=[CH2:13]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][CH:12]([CH2:11][OH:14])[O:10][N:9]=2)=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Bromo-pyridine-2-carbaldehyde oxime (60 g, 298.5 mmol) and allyl alcohol (49.7 ml) were added to tetrahydrofuran (200 ml) and then bleach (2016 ml) was added. The reaction was stirred for four hours followed by extraction with tetrahydrofuran (2×200 ml). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (38.8 g).
Workup
- additionwas added
- extractionfollowed by extraction with tetrahydrofuran (2×200 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5f60ec7388bc4a3c8b627aada4cdbde8
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07396847B2
Reaction notes
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