Water → HCID 178516523, compound

HRID 384453Notes

Reaction equation

C1(C)C=CC(S([O:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.[OH:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[O:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][O:10][C:25]2[CH:24]=[CH:23][N:22]=[C:21]([OH:20])[CH:26]=2)[CH2:18][CH2:17]1.[O:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][O:10][C:21]2[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][N:22]=2)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(tetrahydro-2H-pyran-4-yl)ethyl p-toluenesulfonate (465 mg) in DMF (5 mL) were added 2,4-dihydroxypyridine (363 mg) and potassium carbonate (339 mg), and the mixture was stirred at 80° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and water (50 mL) was added thereto, followed by extraction with ethyl acetate (20 mL×3). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methanol/chloroform=0/100˜10/90) to obtain 4-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]pyridin-2-ol (160 mg) as a major product, and 2-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]pyridin-4-ol (Production Example 347) (43 mg) as a minor product.

Workup

temperatureto cool to room temperature
extractionfollowed by extraction with ethyl acetate (20 mL×3)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: methanol/chloroform=0/100˜10/90)

Sources & evidence

ORD record: ord-9e1ac252942f4d15b2f54ad073f7f2e8
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367702B2

Reaction notes

Loading…