Sodium Hydroxide → HCID 86718467, compound

HRID 1396648Notes

Reaction equation

HRID 1396648 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[OH-].[Na+].Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([Cl:19])[N:11]=1>C1COCC1>[Cl:19][C:12]1[N:11]=[C:10]([O:6][C@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 852392,6-Dichloro-3-nitropyridineHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 86718467HCID 86718467, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of THF and 320 mg (3.6 mmol) (3S)-tetrahydrofuran-3-ol is cooled to 0° C. and 145 mg (3.6 mmol) NaOH are added and the mixture stirred for 1 h. 700 mg (3.6 mmol) 2,6-dichloro-3-nitro-pyridine are slowly added and the mixture is stirred at RT for 3 days. The reaction mixture is filtered and evaporated The residual is purified by FC, giving rise to 600 mg (68%) 6-chloro-3-nitro-2-[(3S)-tetrahydrofuran-3-yl]oxy-pyridine.

Workup

  1. stirringthe mixture is stirred at RT for 3 days
  2. filtrationThe reaction mixture is filtered
  3. customevaporated The residual
  4. customis purified by FC

Sources & evidence

ORD record
ord-0ba854451a0e44b88674bd220d9cb163
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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