HCID 13600230, compound → HCID 90033029, compound

HRID 1488066Notes

Reaction equation

HRID 1488066 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.[Li]CCCC.[O:20]1[CH2:23][C:22](=[O:24])[CH2:21]1>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:22]2([OH:24])[CH2:23][O:20][CH2:21]2)[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:13])([CH3:12])[CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 13600230HCID 13600230, compound2×HCID 150242543-OxetanoneHCID 178418339Butyllithium

Product 1

HCID 90033029HCID 90033029, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a 1000-mL three-neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (compound 192.1, 9 g, 42.38 mmol) in tetrahydrofuran (200 mL). This was followed by the addition of n-BuLi (34 mL, 2.5 M in THF) dropwise at −78° C. and stirred for 1 h. To this was added a solution of oxetan-3-one (6.11 g, 84.79 mmol) in tetrahydrofuran (30 mL) dropwise at −78° C. The reaction mixture was stirred for 1 h at −78° C., then quenched with 50 mL of NH4Cl (sat.). The aqueous phase was extracted with 1×600 mL of ethyl acetate. The organic layer was washed with 3×300 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 13 g (crude) of the title compound as a light yellow solid.

Workup

  1. customInto a 1000-mL three-neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe reaction mixture was stirred for 1 h at −78° C.
  4. customquenched with 50 mL of NH4Cl (sat.)
  5. extractionThe aqueous phase was extracted with 1×600 mL of ethyl acetate
  6. washThe organic layer was washed with 3×300 mL of brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6182f8135632473e9fe86104c0604d15
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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