Sodium sulfate decahydrate → Furo[3,2-c]pyrazolo[1,5-a]pyridin-1-ylmethanol

HRID 2389875Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:19](OCC)=[O:20])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[C:11]=12.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]1([CH2:19][OH:20])[CH:8]=[N:9][N:10]2[CH:15]=[CH:14][C:13]3[O:16][CH:17]=[CH:18][C:12]=3[C:11]=12

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 80% lithium aluminum hydride (250 mg, 5.40 mmol) in tetrahydrofuran (10 mL) was added a solution of ethyl furo[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate (310 mg, 1.35 mmol) in tetrahydrofuran (10 mL) at room temperature, and the mixture was stirred at 50° C. for 5 min. Sodium sulfate decahydrate (4.3 g) was added under ice-cooling, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) and further washed with diisopropyl ether to give the title compound (125 mg, yield 49%).

Workup

temperaturecooling
filtrationthe insoluble material was filtered off
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate)
washfurther washed with diisopropyl ether

Sources & evidence

ORD record: ord-e29e0cc7eb814cfe95ba802e2a8a1ba9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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