p-Toluenesulfonic acid → 2-Pentadecyn-1-ol

HRID 918986Notes

Reaction equation

HRID 918986 reaction equation
[CH2:1]([O:16]C1CCCCO1)[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH2:1]([OH:16])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 674233292-(pentadec-2-ynyloxy)tetrahydro-2H-pyran

Product 1

HCID 5344292-Pentadecyn-1-olYield 85.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cleavage of the THP ether from crude 2-(pentadec-2-ynyloxy)tetrahydro-2H-pyran (30 g) using PTSA as described above gave pentadec-2-yn-1-ol (18.6 g, 85%) as a colorless oil. TLC: 30% EtOAc/hexanes, Rf≈0.40; 1H NMR (CDCl3, 300 MHz) δ 4.25 (s, 2H), 2.17-2.23 (m, 2H), 1.70 (br s, 1H), 1.40-1.53 (m, 2H), 1.20-1.48 (m, 18H), 0.87 (t, 3H, J=7.3 Hz).

Sources & evidence

ORD record
ord-b59bdb42e45d4825878a2d22a0f95968
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

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