Tetrahydrofuran → HCID 129387551, compound

HRID 2281089Notes

Reaction equation

HRID 2281089 reaction equation
[CH3:1][O:2][C:3](=[O:7])[C@H:4]([OH:6])[CH3:5].C1COCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=1>>[N+:30]([C:29]1[C:24]([O:6][C@H:4]([CH3:5])[C:3]([O:2][CH3:1])=[O:7])=[N:25][CH:26]=[CH:27][CH:28]=1)([O-:32])=[O:31]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 796132-Chloro-3-nitropyridineHCID 637514(+)-Methyl lactateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 129387551HCID 129387551, compound

Conditions

Temperature
60 °C

Procedure

To a solution of 5.3 g (50.5 mmol) (R)-2-Hydroxy-propionic acid methyl ester in THF 50.5 mL (1 M in THF; 50.5 mmol) LiHMDS is added drop wise. After 10 minutes of stirring 4.0 g (25.2 mmol) 2-choro-3-nitro-pyridine is added. The mixture is stirred at 60° C. over night. The solvent is evaporated and the residue take up EtOAc washed with water, dried and evaporated to give rise to methyl (2R)-2-[(3-nitro-2-pyridyl)oxy]propanoate

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. washwashed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-21f718a9b9cc45639487e2af1f4f5ddf
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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