Sodium Bicarbonate → HCID 23103617, compound

HRID 2116498Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[C:16]([O:17]COCC[Si](CC)(CC)CC)=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:5][CH:4]=1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[OH:10])=[CH:7][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-ethylphenyl-[3-[2-(triethylsilyl)ethoxymethoxy]]pyridin-2-yl-methanol (2.35 g, 6.54 mmol) in THF-water (25:1; 60 mL), p-toluenesulfonic acid monohydrate (2.8 g, 16.4 mmol) was added and stirred at room temperature for 20 hours and at 40° C. for 4 hours. After cooling the reaction mixture to room temperature, saturated sodium bicarbonate solution (100 mL) was added and the resulting mixture was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 4-ethylphenyl-3-hydroxypyridin-2-yl-methanol (0.62 g).

Workup

temperatureAfter cooling the reaction mixture to room temperature
extractionthe resulting mixture was then extracted with ethyl acetate
washThe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationAfter the solvent was distilled off under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-092eb62a49484917bc40e88e61630e6d
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439232B2

Reaction notes

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