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

HRID 1263078Notes

Reaction equation

HRID 1263078 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>CCCCCC>[O:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[O:5][CH2:1][CH2:2][C:3]#[CH:4]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OL

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranYield 99.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of 3-butyn-1-ol (3.0 g, 0.042 mol) and 3,4-dihydropyran (4.20 g, 0.05 mol) in hexane (10 ml) (Bongini et. al., Synthesis, 618, 1979), is added to a suspension of Dowex (1.5 g) in hexane (10 ml) and the mixture is stirred for 1 hr at room temperature. The resin is filtered off and the solvent removed in vacuo. The crude residue is purified by flash chromatography using hexane/ethyl acetate (9:1, v/v) to give 3-butyn-1-yl tetrahydropyranyl ether (6.47 g, 97%) as a colorless liquid: Rf=0.25; Hexane/ethyl acetate (1:1, v/v) IR (film) ν3300 (C≡C--H), 2160 (C≡C); and 1H NMR (CDCl3) δ1.48 (m, 6H), 1.88 (t, J=3 Hz, 1H), 2.35 (m, 2H), 3.60 (m, 4H), 4.56 (br S, 1H).

Workup

  1. filtrationThe resin is filtered off
  2. customthe solvent removed in vacuo
  3. customThe crude residue is purified by flash chromatography

Sources & evidence

ORD record
ord-a7de568f58ec4fa4a73aa3a2c13c368a
Source dataset
uspto-grants-1984_06
Patent number
US04455441

Reaction notes

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