Water → [2-(1H-indazol-5-yloxy)phenyl]methanol

HRID 1269856Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13](OC)=[O:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[CH2:13][OH:14])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

The methyl 2-(1H-indazol-5-yloxy)benzoate (95.6 g, 0.36 mmol) obtained in Example 478 was dissolved in tetrahydrofuran (5 ml), and lithium aluminum hydride (44.1 mg, 1.07 mmol) was added thereto at 0° C. and stirred for 30 minutes. Water (0.3 ml), a 2N-aqueous sodium hydroxide solution (0.6 ml) and water (0.9 ml) was added dropwise thereto in that order, and the precipitate formed was removed by filtration. A saturated aqueous sodium hydrogencarbonate solution was added to the filtrate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to obtain [2-(1H-indazol-5-yloxy)phenyl]methanol (56 mg, 65%).

Workup

customin that order, and the precipitate formed
customwas removed by filtration
additionA saturated aqueous sodium hydrogencarbonate solution was added to the filtrate
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b150459f4b4648c082721edbf6f16c8f
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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