Propargyl bromide → 3-(2-Oxo-1,3-oxazolin-3-yl)-1-propyne

HRID 1369105Notes

Reaction equation

HRID 1369105 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]#[CH:11].[OH:12]S([O-])(=O)=O.[K+]>C1COCC1>[O:12]=[C:2]1[N:3]([CH2:9][C:10]#[CH:11])[CH:4]=[CH:5][O:1]1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 68157OxazolineHCID 516920Potassium bisulfate

Product 1

HCID 119878593-(2-Oxo-1,3-oxazolin-3-yl)-1-propyneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 2-oxazoline (1.0 g, 11.5 mmol) in THF (40 mL) was added 60% NaH (460 mg, 11.5 mmol) and 3-bromopropyne (1. 0 mL, 11.2 mmol). The mixture was stirred for 1 h at 50° C. then for 3 h at 60° C., poured into aqueous 5% KHSO4, and extracted with ethyl acetate. The Organic layers were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 1:1 hexane/ethyl acetate to give the title compound (1.02 g, 71%).

Workup

  1. waitfor 3 h at 60° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe Organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c2db30b8e0a543ecbcdce778a32373a8
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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