Tetrahydrofuran → (S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

HRID 2265135Notes

Reaction equation

HRID 2265135 reaction equation
O1CCCC1.[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[NH:10]1)([CH3:8])[CH3:7].[C:15](Cl)(=[O:20])[CH2:16][CH2:17][CH:18]=[CH2:19]>O>[CH:6]([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[N:10]1[C:15](=[O:20])[CH2:16][CH2:17][CH:18]=[CH2:19])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 42284934-Pentenoyl chlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 11820460(S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

Tetrahydrofuran (2 L) solution of 108 g of (S)-4-isopropyl-oxazolidin-2-one was cooled in a dry ice bath at −70° C., 345 mL of 2.66 M n-butyllithium-hexane solution was added thereto, and the reaction liquid was stirred at −70° C. for 30 minutes. Next, 102 mL of 4-pentenoyl chloride was added thereto at −70° C., the reaction liquid was stirred for 30 minutes, and water was added thereto to stop the reaction. This was extracted with ethyl acetate, the organic layer was washed with aqueous saturated sodium deuteride solution, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure to obtain a crude product of the entitled compound.

Workup

  1. addition345 mL of 2.66 M n-butyllithium-hexane solution was added
  2. customthe reaction liquid
  3. customat −70° C., the reaction liquid
  4. stirringwas stirred for 30 minutes
  5. customthe reaction
  6. extractionThis was extracted with ethyl acetate
  7. washthe organic layer was washed with aqueous saturated sodium deuteride solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-54818e95b0944f7d955994779716be83
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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