Sodium Iodide → 1-Iodo-4-phenoxybut-2-yne

HRID 652118Notes

Reaction equation

HRID 652118 reaction equation
CS(O[CH2:6][C:7]#[C:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.S([O-])(=O)(=O)C.[I-:22].[Na+].C(=O)(O)[O-].[Na+]>CC(C)=O>[I:22][CH2:6][C:7]#[C:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 22126265HCID 22126265, compound

Product 1

HCID 198494611-Iodo-4-phenoxybut-2-yne

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

By following the esterification method of part B of this preparation, the preceding compound was converted into 4-phenoxybut-2-yn-1-ol methanesulfonate in almost quantitative yield. The foregoing crude mesylate was dissolved in 15 ml of acetone and treated with a solution of 5.55 g (0.037 mol) of sodium iodide and 1.049 g (0.0123 mol) of sodium bicarbonate in 30 ml of acetone. The reaction mixture was stirred for 1 hour at room temperature and then the solvent was removed under reduced pressure. The residue was diluted with water and extracted with methylene chloride; the organic extracts were dried and evaporated. The residue was purified by silica gel column chromatography using hexane-ethyl acetate (95:5) as eluant, to yield 1-iodo-4-phenoxybut-2-yne.

Workup

  1. customthe esterification method of part B of this preparation
  2. customthe solvent was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. customthe organic extracts were dried
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-15b486ed5b37459fb030d4a3a355249f
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Reaction notes

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