Sodium Hydroxide → HCID 58423901, compound

HRID 2096523Notes

Reaction equation

HRID 2096523 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CCO.O.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][CH:10]([C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)[CH2:9][C:8]2=[O:17]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 15354666HCID 15354666, compound

Product 1

HCID 58423901HCID 58423901, compoundYield 51.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(pyridin-4-yl)prop-2-en-1-one (20 g, 63.3 mmol) in EtOH (160 mL) and H2O (480 mL) was added NaOH (2.53 g, 63.3 mmol). The reaction mixture was stirred overnight. The mixture was filtered to give a solid residue. The solid residue was dissolved in EtOAc. The resulting solution was dried over Na2SO4 and concentrated in vacuo to give 6-bromo-2-(pyridin-4-yl)chroman-4-one (10 g, 50%). 1H-NMR (CDCl3): 3.00 (t, 2H), 5.51 (dd, 1H), 7.02 (d, 1H), 7.39 (d, 2H), 7.63 (t, 1H), 8.04 (s, 1H), 8.72 (d, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. customto give a solid residue
  3. dry with materialThe resulting solution was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4685b839e4554904b39d8fe3706c9326
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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