Sodium hydride → HCID 61286363, compound

HRID 1396646Notes

Reaction equation

HRID 1396646 reaction equation
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.Cl[C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[C:13]([Cl:20])[N:12]=1>C1COCC1.CCOC(C)=O.O>[Cl:20][C:13]1[N:12]=[C:11]([O:9][CH:6]2[CH2:7][CH2:8][O:3][CH2:4][CH2:5]2)[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 61286363HCID 61286363, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of THF and 2.4 g NaH (55% in mineral oil, 55 mmol) is cooled to 0° C., 5.2 ml tetrahydro-pyran-4-ol (55 mmol) are slowly added and the mixture stirred for 30 minutes. 10.0 g (52 mmol) 2,6-dichloro-3-nitro-pyridine in THF are slowly added and the mixture is stirred at RT over night. The reaction mixture is diluted with EtOAc and water. The organic phase is separated and washed with water and brine, dried and evaporated. The residual is purified by FC, giving rise to 7.8 g (58%) 6-chloro-3-nitro-2-(tetrahydro-pyran-4-yloxy)-pyridine.

Workup

  1. stirringthe mixture is stirred at RT over night
  2. customThe organic phase is separated
  3. washwashed with water and brine
  4. customdried
  5. customevaporated
  6. customThe residual is purified by FC

Sources & evidence

ORD record
ord-d1d0c423fac244a1bc4c9f790ad8e535
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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