Hydrochloric Acid → HCID 59378455, compound

HRID 888555Notes

Reaction equation

HRID 888555 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.C(N(CC)CC)C.Cl.[F:20][C:21]([F:29])([F:28])[CH:22]([CH2:26][CH3:27])[CH2:23][CH2:24][OH:25]>O1CCCC1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:25][CH2:24][CH2:23][CH:22]([C:21]([F:29])([F:28])[F:20])[CH2:26][CH3:27])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 866429761-Pentanol, 3-(trifluoromethyl)-2×

Product 1

HCID 59378455HCID 59378455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 3-(trifluoromethyl)-1-pentanol in diethyl ether obtained in Step 4 and 26.8 g of p-toluenesulfonyl chloride were dissolved in 300 ml of tetrahydrofuran. To the solution was added dropwise 20 ml of triethylamine at room temperature, and stirred at the same temperature for 4 days. To the reaction mixture was added 10% hydrochloric acid, and then extracted with ethyl acetate. The organic layer was sequentially washed with 10% hydrochloric acid and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel chromatography to obtain 18.4 g of 3-trifluoromethyl-pentyl p-toluenesulfonate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with 10% hydrochloric acid
  3. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d306ea53ec046f59e92a68bdb078e4d
Source dataset
uspto-grants-2012_08
Patent number
US08247612B2

Reaction notes

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