Hydrochloric Acid → HCID 14533171, compound

HRID 2073636Notes

Reaction equation

HRID 2073636 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-1283f4e4b2e64b5180dc894082421eed
Source dataset
uspto-grants-1990_04
Patent number
US04918213

Reaction notes

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