Water → HCID 22033501, compound

HRID 1506159Notes

Reaction equation

HRID 1506159 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(CC)CC)C.O>O1CCCC1>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:1][CH2:2][CH2:3][C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 28008154-(2-Hydroxyethyl)benzonitrile

Product 1

HCID 22033501HCID 22033501, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Hydroxyethyl)benzonitrile (200 mg, 1.35 mmol) in tetrahydrofuran (4 mL) was mixed with 4-methylbenzene-1-sulfonyl chloride (389 mg, 2.04 mmol) and triethylamine (569 μL, 4.08 mmol) and stirred at room temperature for 1 day. After addition of water, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1→3/1→1/1 (v/v)) to give the title compound as a colorless solid (174 mg, yield 43%).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1→3/1→1/1 (v/v))

Sources & evidence

ORD record
ord-06a7f134637b464281ab0a422bc38782
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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