p-Toluenesulfonic acid → Pentadeca-5,14-diyn-1-ol

HRID 918970Notes

Reaction equation

HRID 918970 reaction equation
[CH2:1]([O:16]C1CCCCO1)[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([OH:16])[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 866652612-(Pentadeca-5,14-diynyloxy)tetrahydropyran

Product 1

HCID 86665262Pentadeca-5,14-diyn-1-olYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the 2-(pentadeca-5,14-divnyloxy)tetrahydropyran (4.05 g, 13.27 mmol) and p-toluenesulphonic acid (42 mg) in MeOH (100 mL) was stirred at room temperature for 4 h. All volatiles were then removed in vacuo and the residue was purified by SiO2 column chromatography using 15% EtOAc/hexanes as eluent to give pentadeca-5,14-diyn-1-ol (2.77 g, 95%) as a colorless oil. TLC: 30% EtOAc/hexanes, Rf≈0.40; 1H NMR (300 MHz, CDCl3) δ 3.85 (t, 2H, J=7.0 Hz), 2.03-2.30 (m, 6H), 1.93 (t, 1H, J=2.6 Hz), 1.26-1.83 (m, 14H).

Workup

  1. customAll volatiles were then removed in vacuo
  2. customthe residue was purified by SiO2 column chromatography

Sources & evidence

ORD record
ord-5a1832671c8f47ae9345d35caa21e9cb
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

Loading…