4-Toluenesulfonyl chloride → pent-4-ynyl tosylate

HRID 527192Notes

Reaction equation

HRID 527192 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].CCN(CC)CC>CN(C1C=CN=CC=1)C>[CH3:14][C:13]1[CH:15]=[CH:16][C:10]([S:7]([O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5])(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 793464-Pentyn-1-ol

Product 1

HCID 10966564pent-4-ynyl tosylateYield 74%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

This compound was synthesized as a colorless oil from pent-4-yn-1-ol (145.0 mg, 132 mmol), TsCl (426.3 mg, 2.24 mmol), Et3N (349.4 mg, 3.44 mmol), and DMAP (210.1 mg, 1.72 mmol) in 74% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3, δH) 7.77 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H), 4.24-3.97 (m, 2H), 2.42 (s, 3H), 2.23 (td, J=6.9, 2.6 Hz, 2H), 1.99-1.67 (m, 3H); 13C NMR (100 MHz, CDCl3, δH) 145.06, 133.09, 130.09, 128.12, 82.33, 69.68, 68.98, 27.91, 21.85, 14.90. ESI-MS: 239.1 (M+H+), 261.1 (M+Na4).

Sources & evidence

ORD record
ord-783211168a1e4e2bb0b3f80d438e22aa
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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