Tetrahydrofuran → HCID 117774754, compound

HRID 2281087Notes

Reaction equation

HRID 2281087 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[Li+].C[Si]([N-:11][Si](C)(C)C)(C)C.F[C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=1.[CH3:26][CH2:27][O:28]C(C)=O>Cl.O.N>[CH3:5][C:1]1[CH:2]=[C:3]([C@H:27]([O:28][C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH3:26])[O:4][N:11]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 27628172-Fluoro-3-nitropyridine

Product 1

HCID 117774754HCID 117774754, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 0.3 g (2.44 mmol) 1(1R)-1-(3-methylisoxazol-5-yl)ethanol in THF 2.45 mL (1 M in THF; 2.45 mmol) LiHMDS is added drop wise. After 30 minutes of stirring 0.3 g (2.04 mmol) 2-fluoro-3-nitro-pyridine is added. The mixture is stirred over night. The mixture is diluted with 1 N HCl and water and neutralized with NH3. EtOAc is added and the organic layer is separated, washed with brine, dried and evaporated to furnish 3-methyl-5-[(1R)-1-[(3-nitro-2-pyridyl)oxy]ethyl]isoxazole.

Workup

  1. additionis added
  2. customthe organic layer is separated
  3. washwashed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-c870b547a1794d9094634d87bdd7ba33
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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