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

HRID 2251597Notes

Reaction equation

[OH:1][CH:2]([C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1)[C:3]1[CH:4]=[C:5]([C:24]([OH:26])=[O:25])[C:6]2[O:10][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:7]=2[CH:23]=1>CC(C)=O.CS(C)=O>[C:17]1([C:9]2([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:8][C:7]3[CH:23]=[C:3]([C:2]([C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)=[O:1])[CH:4]=[C:5]([C:24]([OH:26])=[O:25])[C:6]=3[O:10]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 6-(hydroxy-pyridin-4-yl-methyl)-2,2-diphenyl-1,3-benzodioxole-4-carboxylic acid (128 mg, 0.324 mmol, 1 eq.) in a mixture of 10 mL acetone and 3 mL DMSO, IBX (273 mg, 0.973 mmol, 3 eq.) was added and the reaction mixture was stirred 3 h at 50° C. The mixture was partitioned between H2O and EtOAc, and the organic layer was washed with saturated NaCl solution before being dried over MgSO4 and evaporated under reduced pressure to yield the title compound as a yellowish solid.

Workup

additionwas added
customThe mixture was partitioned between H2O and EtOAc
washthe organic layer was washed with saturated NaCl solution
dry with materialbefore being dried over MgSO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-5fc454b0a6ad4f30b57e7655f413f8e1
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319101B2

Reaction notes

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