4-Toluenesulfonyl chloride → HCID 12608696, compound

HRID 527193Notes

Reaction equation

HRID 527193 reaction equation
[CH2:1]([OH:7])[CH2:2]/[CH:3]=[CH:4]/[CH2:5][CH3:6].[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9].CCN(CC)CC>CN(C1C=CN=CC=1)C>[CH3:15][C:14]1[CH:16]=[CH:17][C:11]([S:8]([O:7][CH2:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][CH3:6])(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 5284503trans-Hex-3-en-1-ol

Product 1

HCID 12608696HCID 12608696, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

This compound was synthesized as a colorless oil from (E)-hex-3-en-1-ol (130.0 mg, 1.30 mmol), TsCl (322.2 mg, 1.69 mmol), Et3N (196.6 mg, 1.95 mmol), and DMAP (158.8 mg, 1.30 mmol) in 99% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3, δH) 7.74 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H), 5.50 (dtt, J=15.3, 6.3, 1.3 Hz, 1H), 5.27-5.14 (m, 1H), 4.00 (t, J=6.9 Hz, 2H), 2.43 (s, 3H), 2.36-2.23 (m, 2H), 2.03-1.86 (m, 2H), 0.91 (t, J=7.5 Hz, 3H);

Sources & evidence

ORD record
ord-e37826cf99bc4811bd9d8d5fc565a001
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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