Water → HCID 11025995, compound

HRID 275774Notes

Reaction equation

HRID 275774 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:12][C:13]1[C:17]2[C:18]3[O:23][C@@H:22]([CH2:24][OH:25])[CH2:21][O:20][C:19]=3[CH:26]=[CH:27][C:16]=2[S:15][CH:14]=1.O>CN(C)C1C=CN=CC=1.ClCCl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:25][CH2:24][C@@H:22]2[CH2:21][O:20][C:19]3[CH:26]=[CH:27][C:16]4[S:15][CH:14]=[C:13]([Cl:12])[C:17]=4[C:18]=3[O:23]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 15448810HCID 15448810, compound

Product 1

HCID 11025995HCID 11025995, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Dimethylaminopyridine (0.26 g) then 4-toluenesulphonyl chloride (0.40 g) were added to a stirred solution of (S)-9-chloro-2,3-dihydro-2-(hydroxymethyl)thieno[3,2-f][1,4]-benzodioxin (0.49 g) in dichloromethane (20 ml), and the mixture then stirred at ambient temperature for 24 hours. The resulting solution was poured into water (100 ml) and extracted with dichloromethane (150 ml). The resulting organic solution was then washed successively with saturated copper sulphate solution (2×100 ml) and water (100 ml). The solution was dried over sodium sulphate and the solvent evaporated under reduced pressure to give (S)-9-chloro-2,3-dihydrothieno[3,2-f]-1,4-benzodioxin-2-ylmethyl 4-toluene-sulphonate (0.7 g) as a white solid m.p. 169-70° C.

Workup

  1. extractionextracted with dichloromethane (150 ml)
  2. washThe resulting organic solution was then washed successively with saturated copper sulphate solution (2×100 ml) and water (100 ml)
  3. dry with materialThe solution was dried over sodium sulphate
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b459ea7256c642159b5712abd0289b09
Source dataset
uspto-grants-2002_03
Patent number
US06353002B2

Reaction notes

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