4-Toluenesulfonyl chloride → (4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

HRID 973518Notes

Reaction equation

HRID 973518 reaction equation
[OH:1][C@H:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[C:5]#[N:6].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:1][C@H:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[C:5]#[N:6])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 54327812(4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

Product 1

HCID 54083752(4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrileYield 49%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a solution of 186 mg (0.53 mmol) of (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile in 10 ml of pyridine were added a solution of 303 mg (1.6 mmol) of p-toluenesulfonyl chloride in 20 ml of pyridine and 10 mg of DMAP. The resulting mixture was stirred at room temperature overnight. The pyridine was then removed by evaporation under reduced pressure. The residue was separated and purified by column chromatography (hexane/ethyl acetate=4/1), thereby obtaining 130 mg (yield 49%) of (4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile.

Workup

  1. customThe pyridine was then removed by evaporation under reduced pressure
  2. customThe residue was separated
  3. custompurified by column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-caaa7fb22bcb4b298337ad3f9e892a95
Source dataset
uspto-grants-1991_11
Patent number
US05064564

Reaction notes

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