Hydrochloric Acid → HCID 14533171, compound

HRID 1460934Notes

Reaction equation

HRID 1460934 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][CH2:5][OH:6].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:6][CH2:5][CH2:4][CH:3]([C:2]([F:11])([F:12])[F:1])[CH2:7][CH2:8][CH2:9][CH3:10])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14533169HCID 14533169, compound

Product 1

HCID 14533171HCID 14533171, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

In a round bottomed flask, 1.3 g of optically active 3-trifluoromethyl-1-heptanol and 2.3 g of pyridine were placed and cooled with ice, and 1.4 g of p-toluenesulfonyl chloride was added, followed by 4 hours of stirring at 20° C. After the reaction, dilute hydrochloric acid was added, and the mixture was subjected to two times of extraction with diethyl ether. The resultant ether layer was neutralized by washing with water, dried with magnesium sulfate and purified by silica gel column chromatography (developer: hexane/diethyl ether =2/1) to obtain 2.1 g of 3-trifluoromethylheptyl p-toluenesulfonate 2. (Yield: 88%)

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was subjected to two times of extraction with diethyl ether
  4. washby washing with water
  5. dry with materialdried with magnesium sulfate
  6. custompurified by silica gel column chromatography (developer: hexane/diethyl ether =2/1)

Sources & evidence

ORD record
ord-211d040a13ca460f8ef94317b1e49a00
Source dataset
uspto-grants-1991_12
Patent number
US05073306

Reaction notes

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