4-Toluenesulfonyl chloride → HCID 89287715, compound

HRID 2361587Notes

Reaction equation

HRID 2361587 reaction equation
[CH3:1][CH:2]([CH:9]=[CH2:10])[CH2:3][CH2:4][CH2:5][C@H:6]([OH:8])[CH3:7].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O:8][C@@H:6]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH:9]=[CH2:10])[CH3:7])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86685799HCID 86685799, compound

Product 1

HCID 89287715HCID 89287715, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of (2R)-6-methyloct-7-en-2-ol (12 g, 84 mmol) in pyridine (16 mL) was added DMAP (0.51 g, 4.22 mmol) and the solution was stirred for 10 min. P-Toluenesulfonyl chloride (18.5 g, 97 mmol) 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 bicarbonate solution, brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure to get crude compound (14.5 g, 32%). The crude compound was taken to the next step without further purification.

Workup

  1. customto come to room temperature
  2. stirringstirred overnight
  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 bicarbonate solution, brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81314491af91438c82ee09aaf0145213
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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