2-Pentadecyn-1-ol → Pentadec-14-yn-1-ol

HRID 918987Notes

Reaction equation

[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].[H-].[Na+].C(N)CN>>[CH2:1]([OH:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15]

Participants

Reactant 2

HCID 5344292-Pentadecyn-1-ol

HCID 86665267NaH ethylenediamine

Product 1

HCID 10977125Pentadec-14-yn-1-olYield 76.2%

Procedure

Isomerization of pentadec-2-yn-1-ol (12.5 g, 54.95 mmol) using NaH/ethylenediamine as described above furnished pentadec-14-yn-1-ol (9.4 g, 76%) as a white solid. M.P.: 54.2-54.8° C. TLC: 30% EtOAc/hexanes, Rf≈0.45; 1H NMR (400 MHz, CDCl3) δ 3.60-3.65 (m, 2H), 2.16 (dt, 2H, J=7.1 Hz, 2.4 Hz), 1.92 (t, 1H, J=2.4 Hz), 1.47-1.60 (m, 4H), 1.22-1.35 (m, 18H).

Sources & evidence

ORD record: ord-a2efdbe5ec4d47f483d3984db8374081
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09272991B2

Reaction notes

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