p-Toluenesulfonic acid → 4-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

HRID 652114

Reaction equation

HRID 652114 reaction equation
[CH2:1]([OH:6])[C:2]#[C:3][CH2:4][OH:5].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C(N(CC)CC)C>O1CCCC1>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:5][CH2:4][C:3]#[C:2][CH2:1][OH:6]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80662-Butyne-1,4-diolHCID 80803,4-dihydro-2H-pyranHCID 8471Triethylamine

Product 1

HCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 90 g (1.07 mol) of 2-butyne-1,4-diol and 9 g of p-toluenesulfonic acid in 1000 ml of tetrahydrofuran, cooled to 0° C., there were added dropwise 104.88 ml (96.69 g, 1.15 mol) of dihydropyran, and thereafter the reaction mixture was stirred for 3 hours at room temperature. It was then neutralized with triethylamine and evaporated in vacuo. The residue was purified by silica gel column chromatography (2000 g) using hexane-ethyl acetate (80:20) as eluant, to yield 2-butyne-1,4-diol monotetrahydropyranyl ether and a small amount of the bis-tetrahydropuranyl ether.

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by silica gel column chromatography (2000 g)

Sources & evidence

ORD record
ord-cf7836657d394dc5b655d8618611ccb7
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Linked notes

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