4-Toluenesulfonyl chloride → 2-Pentanol, 2-(4-methylbenzenesulfonate)

HRID 527181Notes

Reaction equation

HRID 527181 reaction equation
[CH3:1][CH:2]([OH:6])[CH2:3][CH2:4][CH3:5].[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>[S:7]([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)([O:6][CH:2]([CH2:3][CH2:4][CH3:5])[CH3:1])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 223862-Pentanol

Product 1

HCID 997532-Pentanol, 2-(4-methylbenzenesulfonate)Yield 92%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

This compound was synthesized as a colorless oil from 2-pentanol (122.0 mg, 1.384 mmol), TsCl (316.6 mg, 1.66 mmol), Et3N (280.3 mg, 2.77 mmol), and DMAP (169.0 mg, 1.384 mmol) in 92% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3; δH) 7.75 (d, J=8.3 Hz, 2H), 7.30 (d, J=8.3 Hz, 2H), 4.63-4.51 (m, 1H), 2.40 (s, 3H), 1.56 (dddd, J=14.0, 10.0, 7.2, 5.4 Hz, 1H), 1.49-1.35 (m, 1H), 1.35-1.04 (m, 5H), 0.77 (t, J=1A Hz, 3H); 13C NMR (100 MHz, CDCl3, δC) 144.57, 134.63, 129.84, 127.78, 80.55, 38.70, 21.73, 20.90, 18.28, 13.74. ESI-MS: 243.1 (M+H+), 265.1 (M+Na+).

Sources & evidence

ORD record
ord-e73433f10b054755a1924a83896cc109
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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