p-Toluenesulfonic acid → Undec-2-yn-1-ol

HRID 2255027Notes

Reaction equation

HRID 2255027 reaction equation
[CH2:1]([O:12]C1CCCCO1)[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([OH:12])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 152326042-[(Undec-2-yn-1-yl)oxy]oxane

Product 1

HCID 182209Undec-2-yn-1-olYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tetrahydro-2-(2-undecynyloxy)-2H-pyran in methanol (100 mL), was added p-toluenesulfonic acid (30 mg). The mixture was stirred at room temperature for 4 hours. The solvent was removed by rotary evaporation. The residue was taken up in ether (150 mL) and washed with aqueous saturated NaHCO3 (120 mL), saturated NaCl (120 mL) and water (200 mL). The organic layer was dried (MgSO4) and concentrated to yield a yellow oil. Purification by flash silica gel chromatography (90:10 hexane/EtOAc) afforded 2-undecyn-1-ol (48) (2.6 g, 77% overall) as a colorless oil: Rf 0.27 (90:10 hexane/EtOAc); IR (neat) 3300, 2925, 2855, 1437, 1110 Cm-1 ; 1H NMR (CDCl3) δ 4.18 (t, J=2.4 Hz, 2 H), 2.8 (s, 1 H), 2.14 (tt, J1 =7.2 Hz, J2 =2.4 Hz, 2 H), 1.35 (m, 12 H), 0.82 (t, J=6.9 Hz, 3 H); 13C NMR (CDCl3) δ 86.15, 78.28, 50.93, 31.76, 29.09, 29.04, 28.82, 28.56, 22.56, 18.63, 13.95. ##STR22##

Workup

  1. customThe solvent was removed by rotary evaporation
  2. washwashed with aqueous saturated NaHCO3 (120 mL), saturated NaCl (120 mL) and water (200 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customto yield a yellow oil
  6. customPurification by flash silica gel chromatography (90:10 hexane/EtOAc)

Sources & evidence

ORD record
ord-5ab9ea51990c4b02b430deece23d723f
Source dataset
uspto-grants-1993_08
Patent number
US05238832

Reaction notes

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