Solketal → HCID 54291342, compound

HRID 1752212Notes

Reaction equation

HRID 1752212 reaction equation
C[C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.CC([O-])(C)C.[K+].Br[C:17]1[CH:22]=[CH:21]C=C[N:18]=1>C1COCC1.O>[N:18]1[CH:17]=[CH:22][CH:21]=[CH:9][C:2]=1[O:3][CH2:4][CH:5]([OH:6])[CH2:7][OH:8]

Participants

6

Reactant 3

HCID 7528SolketalHCID 79732-BromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 54291342HCID 54291342, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Following a literature procedure2, a solution of solketal (1.25 mL, 0.01 mol) in THF (20 mL) was stirred and cooled to 0° C. under N2 and KOtBu (1.349 g, 0.012 mol) was added. The mixture was stirred 15 min, 2-bromopyridine (1.1 mL, 0.011 mol) was added, and the mixture was stirred 18 h at room temperature, diluted with H2O, and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), filtered, and evaporated to give the crude title product (288.1 mg, 17%).

Workup

  1. stirringthe mixture was stirred 18 h at room temperature
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f753a36519eb4c2aa1ff3b2a8f527111
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

Loading…