Lithium Hexamethyldisilazide → HCID 67946452, compound

HRID 2249165Notes

Reaction equation

HRID 2249165 reaction equation
[CH3:1][C:2]1([CH3:22])[O:7][C:6]2[CH:8]=[CH:9][C:10]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])=[CH:11][C:5]=2[CH:4]2[O:21][CH:3]12.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[N+:30]([C:27]1[CH:28]=[CH:29][C:24](=[O:23])[N:25]([C@H:4]2[C@H:3]([OH:21])[C:2]([CH3:1])([CH3:22])[O:7][C:6]3[CH:8]=[CH:9][C:10]([S:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)(=[O:14])=[O:13])=[CH:11][C:5]2=3)[CH:26]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 14517463HCID 14517463, compoundHCID 178526703HCID 178526703, compound

Product 1

HCID 67946452HCID 67946452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.00 g (12.6 mmol) of 3,4-dihydro-2,2-dimethyl-3,4-epoxy-6-(phenylsulfonyl)-2H-benzo[b]pyran and 1.77 g (12.6 mmol) of 2-hydroxy-5-nitropyridine are suspended in a little absolute THF, and 16.7 ml (12.6 mmol) of a 1 M solution of lithium bis-trimethylsilylamide are added dropwise under argon with stirring and ice cooling. The mixture is stirred at room temperature for a further 72 hours, hydrolyzed and extracted three times with ethyl acetate. The combined organic extracts are washed with water and saturated sodium chloride solution and dried over sodium sulfate. The solvent is evaporated in vacuo and the residue is chromatographed on silica gel (ethyl acetate/ cyclohexane 1:1). The compound can be crystallized in ethyl acetate.

Workup

  1. additionare added dropwise under argon
  2. stirringThe mixture is stirred at room temperature for a further 72 hours
  3. extractionhydrolyzed and extracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated in vacuo
  7. customthe residue is chromatographed on silica gel (ethyl acetate/ cyclohexane 1:1)
  8. customThe compound can be crystallized in ethyl acetate

Sources & evidence

ORD record
ord-23646ecd009043c1919f4423a50c13ab
Source dataset
uspto-grants-1991_08
Patent number
US05043344

Reaction notes

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