3-Methoxy-1-butanol → 3-Methoxybutyl 4-(trifluoromethyl)benzenesulfonate

HRID 1886753Notes

Reaction equation

HRID 1886753 reaction equation
[CH3:1][O:2][CH:3]([CH3:7])[CH2:4][CH2:5][OH:6].[F:8][C:9]([F:21])([F:20])[C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1.C(OCC)(=O)C>[F:21][C:9]([F:8])([F:20])[C:10]1[CH:11]=[CH:12][C:13]([S:16]([O:6][CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH3:7])(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 172913-Methoxy-1-butanolHCID 27773994-(Trifluoromethyl)benzenesulfonyl chloride

Product 1

HCID 867619773-Methoxybutyl 4-(trifluoromethyl)benzenesulfonateYield 42.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxybutane-1-ol (12) (0.58 g, 4.9 mmol) in pyridine (5 mL) was added p-(trifluoromethyl)-benzenesulfonyl chloride (0.98 g, 4 mmol). The solution was stirred at rt for 3.5 h. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with 1 M HCl (6×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL). The organics were dried over Na2SO4 and concentrated to give an oil (13) (0.53 g, 40%). 1H NMR (400 MHz CDCl3) δ 8.03 (d, 2H, J=8.1 Hz), 7.81 (d, 2H, J=8.3 Hz), 4.19 (m, 2H), 3.35 (m, 1H), 3.18 (s, 3H), 1.78 (m, 2H), 1.09 (d, 3H, J=6.0 Hz); 19F δ (s). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 45.99; H, 4.64.

Workup

  1. washwashed with 1 M HCl (6×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL)
  2. dry with materialThe organics were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2b0b95575fcd4d4ea8796de5eb95f84b
Source dataset
uspto-grants-2013_08
Patent number
US08501382B1

Reaction notes

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