Potassium tert-butoxide → 3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-ol

HRID 1363175Notes

Reaction equation

HRID 1363175 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[C:13]([CH:14]([OH:18])[CH2:15][CH2:16][OH:17])=[CH:12][CH:11]=[CH:10][N:9]=1>C(O)(C)(C)C>[O:17]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[CH:14]([OH:18])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 598465701-(2-Chloropyridin-3-yl)propane-1,3-diol

Product 1

HCID 230491373,4-dihydro-2H-pyrano[2,3-b]pyridin-4-olYield 88.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (0.88 g) was added to a solution of 1-(2-chloropyridin-3-yl)propane-1,3-diol (0.49 g) in tert-butanol and the solution was heated at reflux for 3 hr, allowed to cool to RT, quenched via the addition al of sat. NH4Cl (2 mL), solvents reduced then silica gel added and remaining solvents removed in vacuo. The material was added to a silica gel column that was eluted with EtOAc and 1% MeOH/EtOAc to yield the titled product (0.35 g) NMR CDCl3 1H δ 8.1 (dd, 1H), 7.7 (dd, 1H), 6.9 (dd, 1H), 4.9 (dd, 1H), 4.5 (m, 2H), 2.1 (m, 2H); MH+=152.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 3 hr
  3. customquenched via the addition al of sat. NH4Cl (2 mL), solvents
  4. additionsilica gel added
  5. customremoved in vacuo
  6. additionThe material was added to a silica gel column that
  7. washwas eluted with EtOAc and 1% MeOH/EtOAc

Sources & evidence

ORD record
ord-4f99c3c2360f43de9a3e086f610f9bf1
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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