Ethyl Acetate → HCID 86761978, compound

HRID 1886755Notes

Reaction equation

HRID 1886755 reaction equation
[CH3:1][C:2]([OH:7])([CH3:6])[CH2:3][CH2:4][OH:5].[F:8][C:9]([F:21])([F:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17].C(OCC)(=O)C>C(Cl)Cl>[F:21][C:9]([F:8])([F:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([O:5][CH2:4][CH2:3][C:2]([OH:7])([CH3:6])[CH3:1])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 247470Isopentyldiol

Product 1

HCID 86761978HCID 86761978, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-methyl-1,3-butane diol (2.5 g, 21 mmol) and TEA (1.63 g, 16 mmol) in CH2Cl2 (15 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (2.03 g, 8.3 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at rt for 7 h. The reaction mixture was diluted with CH2Cl2 (75 mL) and washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography with ethyl acetate in hexanes yielded the desired product (1.73 g, 66%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.75 (m, 2H), 4.32 (t, 2H, J=7.0 Hz), 1.91 (t, 2H, J=7.0 Hz) 1.22 (s, 6H). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 45.73; H, 4.88.

Workup

  1. washwashed with 1 M HCl (2×25 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
  4. customto give a crude mixture

Sources & evidence

ORD record
ord-25dfd69f2fae4346a419888c8bd084b6
Source dataset
uspto-grants-2013_08
Patent number
US08501382B1

Reaction notes

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