Iodoethane → 2-Pent-2-ynyloxy-tetrahydro-pyran

HRID 2052579Notes

Reaction equation

HRID 2052579 reaction equation
[H-].[Na+].[CH2:3](I)[CH3:4].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][C:14]#[CH:15].[H][H].[Cl-].[NH4+]>O.C1COCC1>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][CH2:13][C:14]#[C:15][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418361HCID 178418361, compound

Product 1

HCID 155618322-Pent-2-ynyloxy-tetrahydro-pyran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

THF (2 ml) is added to 68 mg of sodium hydride (content: 47%), and 293 mg of ethyl iodide and 100 mg of the propargyl tetrahydropyranyl ether obtained as above is added to the mixture. The resulting mixture is refluxed for 12 hours and then cooled to room temperature. Several droplets of water are added to the mixture. After the evolution of hydrogen gas has ceased, one ml of 10% aqueous solution of ammonium chloride is added to the reaction mixture, and the mixture is then extracted with ether. The solvent is distilled off, and the residue is further distilled in a vacuum, giving 2-pentynyl tetrahydropyranyl ether, the desired product. The yield resulting from purification by column chromatography (SiO2) is 94%, b.p. 110°-113° C./17 mm Hg. (In the following examples, the product will be purified similarly.)

Workup

  1. customobtained
  2. additionas above is added to the mixture
  3. temperatureThe resulting mixture is refluxed for 12 hours
  4. extractionthe mixture is then extracted with ether
  5. distillationThe solvent is distilled off
  6. distillationthe residue is further distilled in a vacuum

Sources & evidence

ORD record
ord-c3c580ea7c7c4e1893f22c65d5961ac7
Source dataset
uspto-grants-1980_01
Patent number
US04186141

Reaction notes

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