4-Toluenesulfonyl chloride → HCID 59557759, compound

HRID 2403754Notes

Reaction equation

HRID 2403754 reaction equation
[F:1][CH:2]([F:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH3:19][C:9]1[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH:2]([F:8])[F:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 534127602-(2,2-Difluoroethoxy)ethan-1-ol

Product 1

HCID 59557759HCID 59557759, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(2,2-difluoroethoxy)ethanol (0.13 g, 1.0 mmol), p-toluenesulfonyl chloride (0.19 g, 1.0 mmol), and DMAP (0.12 g, 1.0 mmol) were dissolved in dichloromethane (2 ml) at 0° C. and stirred for 2 h at this temperature. The reaction mixture was loaded onto a small column, which was eluted with dichloromethane to yield the title compound as a clear oil (53 mg, 19%). It was observed that the size of the column affects reaction yield, with a smaller column giving a better yield. 1H NMR (CDCl3, 300 MHz): δ 7.78 (d, 2H, J=11.2 Hz), 7.34 (d, 2H, J=11.2 Hz), 5.76 (tt, 1H, J1=5.6 Hz, J2=73.6 Hz), 4.17 (t, 2H, J=6.0 Hz), 3.75 (t, 2H, J=6.0 Hz), 3.64 (td, 2H, J1=6.0 Hz, J2=20 Hz), 2.45 (br s, 3H).

Workup

  1. washwas eluted with dichloromethane

Sources & evidence

ORD record
ord-4646f137083e4765adc1b382a4a84cdd
Source dataset
uspto-grants-2014_08
Patent number
US08802637B2

Reaction notes

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