4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

HRID 2082152Notes

Reaction equation

HRID 2082152 reaction equation
C(=C(O)[C@@H](O)[C@@H](O)C=[O:8])(C)C.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C1COCC1>[CH3:22][C:12]1[CH:17]=[CH:16][C:15]([S:18]([OH:8])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 21310054HCID 21310054, compound

Product 1

HCID 6101p-Toluenesulfonic acidYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For example, alcohol 4 was prepared with a 50-65 percent yield by coupling 2,3,-isopropylidene-D-erythrose with the known Wittig reagent (4-carbethoxybutyl) triphenylphosphonium bromide and KN(SiMe3)2 in THF at -78 degrees C. to 0 degrees C. The alcohol 4 was then treated with p-toluenesulfonyl chloride to furnish the corresponding p-toluenesulfonate. This p-toluenesulfonate was treated with sodium azide NaN3 in dimethyl formamide (DMF) (CH3)2NCHO at about 70 degrees C. to 100 degrees C. to produce the imino ester 6 having the structure ##STR11## wherein R is (C1 -C8) alkyl;

Workup

  1. customat -78 degrees C
  2. customto 0 degrees C

Sources & evidence

ORD record
ord-5be70bd6681b4560b4b8cd64d2046d7f
Source dataset
uspto-grants-1993_02
Patent number
US05187279

Reaction notes

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