Lithium Hexamethyldisilazide → HCID 59191368, compound

HRID 1023927Notes

Reaction equation

HRID 1023927 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]([F:20])[C:16](F)([F:18])[F:17])=[CH:11][C:10]=2[O:21][CH3:22])[N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:20])=[C:16]([F:17])[F:18])=[CH:11][C:10]=2[O:21][CH3:22])[N:3]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 59191387HCID 59191387, compound

Product 1

HCID 59191368HCID 59191368, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-fluoro-6-[2-methoxy-4-(1,2,2,2-tetrafluoroethyl)phenoxy]pyridine (0.078 mmol; 25 mg) under argon in THF (1 mL) at 0° C. was added dropwise a one molar solution of LiHMDS in THF (0.094 mmol; 94 μl). The reaction mixture was let come back to rt for 16 h. Concentration and purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70) afforded the title compound (10 mg; 0.033 mmol; 43%).

Workup

  1. concentrationConcentration and purification by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-15f2bef5897541c9b90d01d5598401ab
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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