4-Toluenesulfonyl chloride → HCID 22418852, compound

HRID 374676Notes

Reaction equation

HRID 374676 reaction equation
[CH2:1]1[CH2:21][O:20][C:19]2[C:3](=[C:4]([CH:16]=[CH:17][CH:18]=2)[CH2:5][CH:6]([CH2:14][OH:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[O:2]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[CH2:1]1[CH2:21][O:20][C:19]2[C:3](=[C:4]([CH:16]=[CH:17][CH:18]=2)[CH2:5][CH:6]([CH2:14][O:15][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=2)(=[O:30])=[O:29])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[O:2]1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22418825HCID 22418825, compound

Product 1

HCID 22418852HCID 22418852, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

238 mg of tert-butyl 2-(2,3-ethylenedioxybenzyl)-3-hydroxypropionate was dissolved in 4 ml of dry pyridine, and 170 mg of p-toluenesulfonyl chloride was added thereto. The mixture was reacted at room temperature overnight and then concentrated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate and washed sequentially with 50 ml of a 5% potassium hydrogensulfate aqueous solution, with 50 ml of a 4% sodium hydrogencarbonate aqueous solution and with 50 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to obtain 257 mg of tert-butyl 2-(2,3-ethylenedioxybenzyl)-3-p-toluenesulfonyloxypropionate as colorless transparent syrup.

Workup

  1. customThe mixture was reacted at room temperature overnight
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  4. washwashed sequentially with 50 ml of a 5% potassium hydrogensulfate aqueous solution, with 50 ml of a 4% sodium hydrogencarbonate aqueous solution and with 50 ml of a saturated sodium chloride aqueous solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-616113c51524430b9fa660075d160c16
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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