Nitrogen → HCID 86649487, compound

HRID 2065056Notes

Reaction equation

HRID 2065056 reaction equation
N#N.[C:3]([Si:7]([CH3:17])([CH3:16])[O:8][CH:9]([C:11]1[O:12][CH:13]=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].C([Li])(C)(C)C.CN([CH:26]=[O:27])C.[NH4+].[Cl-]>C1COCC1.CCCCC.CC(=O)OCC.O>[C:3]([Si:7]([CH3:17])([CH3:16])[O:8][CH:9]([C:11]1[O:12][C:13]([CH:26]=[O:27])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4]

Participants

10

Reactant 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 668215482-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 86649487HCID 86649487, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazole (733 mg, 3.22 mmol) in dry THF (16 mL) at −78° C. was treated with t-butyllithium (2.62 mL of a 1.6M solution in pentane, 4.19 mmol) while keeping the temperature below −70° C. The reaction mixture was then stirred for 1 h at −40° C. DMF (0.50 mL, 6.45 mmol) was added dropwise at −78° C. The reaction mixture was allowed to warm up to rt and stirred for 2 h at rt. Water (30 mL) was added followed by sat. aq. NH4Cl (20 mL) and EA (20 mL), the layers separated and the aq. layer extracted with EA (2×30 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:4 EA-Hept) gave the title compound as a colorless oil. TLC: rf (1:4 EA-Hept)=0.33. LC-MS-conditions 02: tR=1.08 min, [M+H]+=256.38.

Workup

  1. customthe temperature below −70° C
  2. temperatureto warm up to rt
  3. stirringstirred for 2 h at rt
  4. customthe layers separated
  5. extractionthe aq. layer extracted with EA (2×30 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (1:4 EA-Hept)

Sources & evidence

ORD record
ord-0743b9f58b7a460e99c124d19001e0fa
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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