4-Pyridinecarboxaldehyde → 6-(Hydroxy-pyridin-4-yl-methyl)-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

HRID 2251596Notes

Reaction equation

HRID 2251596 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:7][C:6]=2[CH:22]=1.O(C)[Li].[N:29]1[CH:34]=[CH:33][C:32]([CH:35]=[O:36])=[CH:31][CH:30]=1>>[OH:36][CH:35]([C:32]1[CH:33]=[CH:34][N:29]=[CH:30][CH:31]=1)[C:2]1[CH:3]=[C:4]([C:23]([OH:25])=[O:24])[C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:7][C:6]=2[CH:22]=1

Participants

4

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 596429946-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acidHCID 178419045HCID 178419045, compound

Product 1

HCID 596429816-(Hydroxy-pyridin-4-yl-methyl)-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid

Procedure

6-Bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid (1 g, 2.52 mmol, 1 eq.), LiOMe (192 mg, 5.04 mmol, 2 eq.) and pyridine-4-carbaldehyde (0.48 mL, 5.03 mmol, 2 eq.) as the electrophile were reacted according to GP4, Method A. The crude product was purified using flash chromatography (silica gel, CH2Cl2/MeOH 92:8→80:20) to give the title compound as a yellow solid.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-9325249496424ae68387ab9111c2d2a2
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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