4-Toluenesulfonyl chloride → HCID 24805800, compound

HRID 1049280Notes

Reaction equation

HRID 1049280 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:7][CH2:6][C:3]2([C:2]([F:9])([F:8])[F:1])[CH2:5][CH2:4]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

Product 1

HCID 24805800HCID 24805800, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A 0° C. solution of (1-(trifluoromethyl)cyclopropyl)methanol (2.46 g, 17.56 mmol), TEA (2.94 mL, 21.1 mmol) and DMAP (0.215 g, 1.76 mmol) in DCM (35 mL) was treated with p-toluenesulfonyl chloride (3.38 g, 17.7 mmol), allowed to warm to RT and stirred overnight. The mixture was treated with additional DCM, washed with 2N HCl (3×), followed by satd. NaHCO3, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford (1-(trifluoromethyl)cyclopropyl)methyl 4-methylbenzenesulfonate (3.42 g, 66%). 1H NMR (400 MHz, DMSO-d6): δ 7.77 (m, 2H), 7.48 (m, 2H), 4.16 (s, 2H), 2.41 (s, 3H), 1.04 (m, 2H), 0.92 (m, 2H); MS (ESI) m/z: 295.1 (M+H+).

Workup

  1. washwashed with 2N HCl (3×)
  2. dry with materialNaHCO3, dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-02bce58988824e0a9cbd3d360d208c6b
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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