Diethyl Sulfate → HCID 19047533, compound

HRID 1780909Notes

Reaction equation

HRID 1780909 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+].C(OS([O:15][CH2:16][CH3:17])(=O)=O)C.C1C[O:21][CH2:20]C1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:21]1[CH:1]=[CH:2][C:3]([CH:4]([O:15][CH2:16][CH3:17])[C:5]#[CH:6])=[CH:20]1

Participants

6

Reactant 4

HCID 6163Diethyl SulfateHCID 8028TetrahydrofuranHCID 8058HexaneHCID 14798Sodium Hydroxide

Product 1

HCID 19047533HCID 19047533, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a mixture of 1-(3-furyl)-1-hydroxy-2-propane (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 (30.0g, 0.195 mol) at 0° C. The mixture was stirred for 3 h at room temperature, poured into ice, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was distilled at 70°-84° C. and (10 mm Hg) to afford 1-(3-furyl-1-ethoxy-2-propyne.

Workup

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

Sources & evidence

ORD record
ord-491a1b04b1054004b4485eb8facf8717
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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