Allyl Alcohol → [3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

HRID 747191Notes

Reaction equation

HRID 747191 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]=1

Participants

4

Reactant 2

HCID 7858Allyl AlcoholHCID 1363756105-Bromopyridine-2-carbaldehyde oxime

Product 1

HCID 17954471[3-(5-Bromopyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. additionwas added
  2. extractionfollowed by extraction with tetrahydrofuran (2×200 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f60ec7388bc4a3c8b627aada4cdbde8
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…