Hydrochloric Acid → HCID 64006143, compound

HRID 333882Notes

Reaction equation

HRID 333882 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:12])[O:8][CH2:9][CH2:10]Cl)([C:4]#[CH:5])[CH3:3].[H-].[Na+].Cl>C1COCC1>[CH3:1][C:2]([N:6]1[CH2:10][CH2:9][O:8][C:7]1=[O:12])([C:4]#[CH:5])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 86670538HCID 86670538, compound

Product 1

HCID 64006143HCID 64006143, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 2-chloroethyl 2-methylbut-3-yn-2-ylcarbamate (1.05 g, 5.5 mmol) was dissolved in dry THF (20 mL) and 60% NaH in oil (665 mg, 16.6 mmol) was added. The mixture was stirred under N2 for 1 day and 5% aq HCl (25 mL) was added. The mixture was extracted with EtOAc (175 mL). The organic layer was washed with brine (25 mL) and dried over Na2SO4. Removal of the solvent left an oil (1.03 g) which was purified by chromatography on a 12-g cartridge eluted with a 0-80% EtOAc in hexanes gradient to afford 3-(2-methylbut-3-yn-2-yl)oxazolidin-2-one (567 mg, 67%) as a white solid. 1H NMR (CDCl3) 1.72 (s, 6H), 2.43 (s, 1H), 3.74 (dd, 2H), 4.18 (dd, 2H).

Workup

  1. extractionThe mixture was extracted with EtOAc (175 mL)
  2. washThe organic layer was washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent
  5. waitleft an oil (1.03 g) which
  6. customwas purified by chromatography on a 12-g cartridge
  7. washeluted with a 0-80% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-69bf4a3666b54c25a83d54aa7e4d0d51
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Reaction notes

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