Diethyl Sulfate → HCID 19047533, compound

HRID 865984Notes

Reaction equation

HRID 865984 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([OH:9])[C:7]#[CH:8])=[CH:2]1.[CH3:10][CH2:11]CCCC.[OH-].[Na+].C(OS(OCC)(=O)=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([O:9][CH2:10][CH3:11])[C:7]#[CH:8])=[CH:2]1

Participants

7

Reactant 4

HCID 6163Diethyl SulfateHCID 8058HexaneHCID 14798Sodium HydroxideHCID 19047560HCID 19047560, compound

Product 1

HCID 19047533HCID 19047533, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(3-furyl)-1-hydroxy-2-propyne (20.0 g, 0.163 mol), hexane (200 mL) and THF (25 mL) was added tetrabutylammonium bromide (1.05 g, 0.0032 mol), 50% NaOH (150 mL) and then diethylsulfate (30.0 g, 0.195 mol) at 0° C. The mixture was stirred for 3 hours at room temperature, poured into ice, and extracted with ethyl acetate. The combined organic layers were wasted with brine, dried over Na2SO4 and concentrated in vacuo. The residue was distilled at 70°-84° C. and (10 mmHg) to afford 1-(3-furyl)-1-ethoxy-2-propyne.

Workup

  1. customat 0° C
  2. additionpoured into ice
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was distilled at 70°-84° C.

Sources & evidence

ORD record
ord-f0d90c9bc07944f1bd6f752552683e57
Source dataset
uspto-grants-1996_10
Patent number
US05569655

Reaction notes

Loading…