Potassium Carbonate → (S)-3-(2-bromopyridine-3-yloxy)-2-methyl-1-propanol

HRID 496812Notes

Reaction equation

[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C@@H:17]([CH3:20])[CH2:18][OH:19]>CC(CC)=O>[Br:1][C:2]1[C:7]([O:8][CH2:16][C@@H:17]([CH3:20])[CH2:18][OH:19])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-bromo-3-pyridinol (230 mg) and potassium carbonate (216 mg) was dissolved in methylethylketone (10 ml) and reacted for 30 minutes. Then, (S)-3-bromo-2-methyl-1-propanol (0.21 ml) was added to the solution and refluxed for 3 hours at 100° C. Potassium carbonate was filtered out and separated by flash chromatography under a silica gel phase (ethyl acetate:normal hexane=1:1). As a result, (S)-3-(2-bromopyridine-3-yloxy)-2-methyl-1-propanol (260 mg, yield: 80%) was obtained.

Workup

customreacted for 30 minutes
filtrationPotassium carbonate was filtered out
customseparated by flash chromatography under a silica gel phase (ethyl acetate:normal hexane=1:1)

Sources & evidence

ORD record: ord-1d4369e11c0b4f37ad8dccad06fee476
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946558B2

Reaction notes

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