Tetrahydrofuran → HCID 15390057, compound

HRID 1952863Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[N:5]=1)[CH3:2].[O:11]1CC[CH2:13][CH2:12]1.C([Li])CCC.[Cl-].[NH4+]>O.CN(C)C(=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:12](=[O:11])[CH3:13])[N:5]=1)[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

16.8 g of 2-ethoxy-6-bromopyridine were introduced into 220 ml of tetrahydrofuran at -75° C. 54.4 ml of n-butyllithium (1.6-molar solution in n-hexane) were added dropwise at this temperature. Stirring was continued for two hours at -75° C., and 7.6 g of N,N-dimethylacetamide were added dropwise at this temperature. The mixture was stirred for a further hour at -75° C. and then warmed to -10° C., and first approximately 170 ml of 20 percent strength aqueous ammonium chloride solution and then 200 ml of water were added dropwise at this temperature. The mixture was extracted 3 times using methyl tert-butyl ether. The combined organic phases were washed 3 times with water and subsequently dried over sodium sulfate. After the solvent had been stripped off, the residue which remained was chromatographed on silica gel using cyclohexane/methyl tert-butyl ether 8:1. This gave 5.5 g of 2-ethoxy-6-acetylpyridine as a colorless solid (m.p.: 36-37° C).

Workup

stirringThe mixture was stirred for a further hour at -75° C.
extractionThe mixture was extracted 3 times
washThe combined organic phases were washed 3 times with water
dry with materialsubsequently dried over sodium sulfate
customthe residue which remained was chromatographed on silica gel

Sources & evidence

ORD record: ord-d62c6ffb6c2d4f1096a989cd42ab1e9a
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114363

Reaction notes

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