Pyridine → (S)-5-methylnon-8-en-3-yl 4-methylbenzenesulfonate

HRID 523188Notes

Reaction equation

HRID 523188 reaction equation
[CH3:1][CH:2]([CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:3][C@@H:4]([OH:7])[CH2:5][CH3:6].N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:7][C@H:4]([CH2:3][CH:2]([CH3:1])[CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:5][CH3:6])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 86683256(S)-5-methylnon-8-en-3-ol

Product 1

HCID 86683255(S)-5-methylnon-8-en-3-yl 4-methylbenzenesulfonateYield 79.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-5-methylnon-8-en-3-ol (9.5 g, 61 mmol) in DCM (100 mL) was added pyridine (20 mL) followed by DMAP (0.74 g, 6.08 mmole) and the solution was stirred for 10 min. p-toluenesulfonyl chloride (17.39 g, 91 mmole) was added to the reaction mass at 0° C. The reaction mass was allowed to come to room temperature and stirred overnight. Solvent was removed under reduced pressure and the residue was diluted with ethyl acetate (100 mL). The organic solution was washed with aqueous 1.5 N HCl solution; saturated bicarbonate solution; brine solution; dried over anhydrous Na2SO4; filtered; and evaporated under reduced pressure to get crude compound (15 g, 79%). The crude compound was taken to the next step without further purification. MS: MS m/z 328.4 (M++18).

Workup

  1. additionwas added to the reaction mass at 0° C
  2. customto come to room temperature
  3. customSolvent was removed under reduced pressure
  4. additionthe residue was diluted with ethyl acetate (100 mL)
  5. washThe organic solution was washed with aqueous 1.5 N HCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customand evaporated under reduced pressure

Sources & evidence

ORD record
ord-85fab28c16b64d49907644953f3c2c38
Source dataset
uspto-grants-2016_05
Patent number
US09334279B2

Reaction notes

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