Diethyl Ether → Tetrahydro-2-(2-propynyloxy)-2H-pyran

HRID 1441038Notes

Reaction equation

HRID 1441038 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1.P(Cl)(Cl)(Cl)=O.C(OCC)C>C(Cl)(Cl)Cl.O>[O:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:4][CH2:1][C:2]#[CH:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7859Propargyl alcoholHCID 80803,4-dihydro-2H-pyranHCID 24813Phosphorus oxychloride

Product 1

HCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of propargyl alcohol (5.6 g.) and dihydropyran (8.4 g.) in chloroform (16 ml.) was stirred in an ice-bath while a solution of phosphorus oxychloride (0.05 ml.) in chloroform (1 ml.) was added. After stirring for 2 hours at 10°-20° diethyl ether and water were added. The ethereal solution was separated and washed with water, saturated sodium carbonate solution and brine, dried over anhydrous magnesium sulphate and evaporated. Distillation yielded prop-2-ynyl tetrahydropyranyl ether (7.0 g., b.p. 68°-71°/25 mm).

Workup

  1. additionwas added
  2. additionwere added
  3. customThe ethereal solution was separated
  4. washwashed with water, saturated sodium carbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customevaporated
  7. distillationDistillation

Sources & evidence

ORD record
ord-af993f1b2c0142f4a1e1faa07caf19cf
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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