Tetrahydrofuran → HCID 117772713, compound

HRID 2281084Notes

Reaction equation

HRID 2281084 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH:7]([OH:9])[CH3:8])[O:4][N:3]=1.C1COCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34]>O.CCOC(C)=O>[F:32][C:30]1[CH:29]=[CH:28][C:27]([N+:33]([O-:35])=[O:34])=[C:26]([CH:31]=1)[O:9][CH:7]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)[CH3:8]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 679672,4-DifluoronitrobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 129202231-(3-Methyl-1,2-oxazol-5-yl)ethan-1-ol

Product 1

HCID 117772713HCID 117772713, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.15 g (32.64 mmol) 1-(3-Methylisoxazol-5-yl)ethanol in THF 32.64 mL (1 M in THF; 32.64 mmol) LiHMDS is added drop wise. After 30 minutes of stirring 5.19 g (32.64 mmol) 2,4-difluoro-1-nitro-benzene is added. The mixture is stirred over night. The mixture is diluted with water and EtOAc. The organic layer is separated, washed with water, dried and evaporated. The residue is purified by FC giving rise to 5-[1-(5-fluoro-2-nitro-phenoxy)ethyl]-3-methyl-isoxazole.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue is purified by FC

Sources & evidence

ORD record
ord-0e11cc3e191f4c6e859ed6acf6623bd2
Source dataset
uspto-grants-2015_09
Patent number
US09139577B2

Reaction notes

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