4-Toluenesulfonyl chloride → HCID 86683232, compound

HRID 1481648Notes

Reaction equation

HRID 1481648 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][CH:9]=[CH2:10])[CH2:3][C@@H:4]([OH:6])[CH3:5].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:6][C@H:4]([CH2:3][CH:2]([CH3:1])[CH2:7][CH2:8][CH:9]=[CH2:10])[CH3:5])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86683230HCID 86683230, compound

Product 1

HCID 86683232HCID 86683232, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of (2S)-4-methyloct-7-en-2-ol (39.0 g, 0.274 moles) in pyridine (400 mL) was added 4-(dimethylamino)pyridine (“DMAP”, 1.67 g, 0.013 moles) and the solution was stirred for 10 min. p-toluenesulfonyl chloride (60 g, 0.315 moles) was added to the reaction mass at 0° C. The reaction mass was allowed to come to room temperature and stirred overnight. Pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (200 mL). The organic solution was washed with aqueous 1.5 N HCl solution, saturated aq. Bicarbonate solution, brine solution, dried over anhydrous Na2SO4, filter, and concentrated under reduced pressure to get crude compound (2S)-4-methyloct-7-en-2-yl 4-methylbenzenesulfonate (54 g, 61%). The crude compound was taken to the next step without further purification.

Workup

  1. additionwas added to the reaction mass at 0° C
  2. customto come to room temperature
  3. customPyridine was removed under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (200 mL)
  5. washThe organic solution was washed with aqueous 1.5 N HCl solution, saturated aq. Bicarbonate solution, brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfilter
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffe4a2c0573b42cf869ff0feb656d8e4
Source dataset
uspto-grants-2016_08
Patent number
US09409943B2

Reaction notes

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