4-Toluenesulfonyl chloride → HCID 24805800, compound

HRID 905981Notes

Reaction equation

HRID 905981 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[F:12][C:13]([F:20])([F:19])[C:14]1([CH2:17][OH:18])[CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:12][C:13]([F:20])([F:19])[C:14]1([CH2:17][O:18][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

Product 1

HCID 24805800HCID 24805800, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonyl chloride (9.6 g, 50.35 mmol) was added at 0° C. to a mixture of (1-trifluoromethyl-cyclopropyl)-methanol (7 g, 49.96 mmol), triethylamine (7.7 mL, 55.24 mmol) and DMAP (0.61 g, 4.996 mmol) in 100 mL of DCM. The resulting mixture was stirred at 0° C. to RT overnight before being washed with aqueous 1M HCl. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 flash chromatography (120 g SiO2, hexanes/[hexanes/Et2O 8/2] 100 to 0% hexanes) to give 7.26 g of toluene-4-sulfonic acid 1-trifluoromethyl-cyclopropylmethyl ester (49% yield).

Workup

  1. washbefore being washed with aqueous 1M HCl
  2. extractionThe aqueous layer was back extracted twice with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by SiO2 flash chromatography (120 g SiO2, hexanes/[hexanes/Et2O 8/2] 100 to 0% hexanes)

Sources & evidence

ORD record
ord-350414da83904f549d161c385da9a23a
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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