Tetrahydrofuran → HCID 15707891, compound

HRID 1607502Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH2:9]([N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.P([O-])(O)(O)=O.[Na+].C1C[O:30][CH2:29]C1>CN(C)C=O>[CH2:9]([N:16]1[CH:20]=[N:19][C:18]([CH:29]=[O:30])=[N:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a continuously stirred mixture of 0.156 moles of lithium diisopropylamide in 150 ml of THF cooled at -70° C. was added dropwise a solution of 1-benzyl-1,2,4-triazole prepared above in 200 ml of THF. After the mixture was stirred for one hour longer, there was added in one portion 16.5 ml of dry dimethylformamide. The mixture was stirred in the cold for 0.5 hour and then at room temperature for 3.5 hours whereupon there was added dropwise a saturated aqueous solution of 21.5 grams of sodium dihydrogenphosphate. After the mixture was extracted well with dichloromethane, the combined extracts were washed with saturated brine, dried over magnesium sulfate, filtered, and evaporated to give a crude product. The crude product was flash column chromatographed over silica gel and eluted with dichloromethane/ethyl acetate (2:1) to provide 24.6 grams of pure 1-benzyl-3-formyl-1,2,4-triazole as a colorless oil.

Workup

stirringThe mixture was stirred in the cold for 0.5 hour
extractionAfter the mixture was extracted well with dichloromethane
washthe combined extracts were washed with saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customto give a crude product
customchromatographed over silica gel
washeluted with dichloromethane/ethyl acetate (2:1)

Sources & evidence

ORD record: ord-e6280a8763a44d7ab64f17a66a196110
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04865837

Reaction notes

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