3,4-dihydro-2H-pyran → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 591692Notes

Reaction equation

HRID 591692 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][C:3]#[CH:4]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OLHCID 21909214Pyridium p-toluenesulfonate

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To but-3-yn-1-ol (40.0 g, 570.0 mmol) and 3,4-dihydro-2H-pyran (48.0 g, 570.0 mmol) in anhydrous dichloromethane (350 mL) was added pyridium p-toluenesulfonate (0.45 g, 1.80 mmol). The mixture was stirred at room temperature for 16 hours. Solvent was evaporated, and the residue was purified by vacuum distillation to give 2-but-3-ynyloxy-tetrahydro-pyran as a light yellow liquid. Yield: 60.0 g (68%).

Workup

  1. customSolvent was evaporated
  2. distillationthe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-a615497ebdd4404ea2839808b235fd3b
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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