Tetrahydrofuran → HCID 19969073, compound

HRID 974709Notes

Reaction equation

HRID 974709 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].O1CCCC1>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:10]([N:7]1[CH:8]=[CH:9][C:4](=[O:3])[CH:5]=[CH:6]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 178418642HCID 178418642, compound

Product 1

HCID 19969073HCID 19969073, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of sodium hydride (2.04 g) in N,N-dimethylformamide (50 ml) was added 4-hydroxypyridine (5 g) at room temperature. Octyl bromide (9.08 ml) was added thereto. The mixture was stirred for 2 hours at 50° C. The reaction mixture was added to a mixture of brine (100 ml), tetrahydrofuran (100 ml) and ethyl acetate (100 ml). The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-octyl-4-pyridone (14.7 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe magnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4e52cd1ca65a48abaf24dd14c128316a
Source dataset
uspto-grants-1997_03
Patent number
USH0001638

Reaction notes

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