p-Toluenesulfonic acid → 2-(Chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

HRID 1673161Notes

Reaction equation

HRID 1673161 reaction equation
CO[C:3]1[CH:7]=[CH:6][S:5][C:4]=1OC.[Cl:10][CH2:11][CH:12]([OH:15])[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:10][CH2:11][CH:12]1[O:15][C:3]2=[CH:4][S:5][CH:6]=[C:7]2[O:14][CH2:13]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 72903-Chloro-1,2-propanediolHCID 14872413HCID 14872413, compound

Product 1

HCID 248536152-(Chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere in a 500 mL round bottom flask equipped with a reflux condenser, 20.0 g (0.139 mol) dimethoxythiophene, 17.8 g (0.161 mol) 3-chloro-1,2-propanediol, and 5 g p-toluenesulfonic acid was dissolved in 350 mL toluene. The reaction was then heated to ˜90 C overnight. At this time TLC indicated consumption of starting material. After cooling the reaction mixture was concentrated to ˜100 mL and poured into saturated potassium carbonate solution. The mixture was extracted with DCM and the combined extracts were dried with magnesium sulfate. Solvent removal gave a dark oil that was purified by column chromatography using 3:1 hexanes/DCM. Solvent removal gave the product as a white solid. Structure and purity were confirmed by 1H/13C NMR and LC-MS.

Workup

  1. customUnder a nitrogen atmosphere in a 500 mL round bottom flask equipped with a reflux condenser
  2. temperatureThe reaction was then heated to ˜90 C overnight
  3. customconsumption of starting material
  4. temperatureAfter cooling the reaction mixture
  5. concentrationwas concentrated to ˜100 mL
  6. additionpoured into saturated potassium carbonate solution
  7. extractionThe mixture was extracted with DCM
  8. dry with materialthe combined extracts were dried with magnesium sulfate
  9. customSolvent removal
  10. customgave a dark oil that
  11. customwas purified by column chromatography
  12. customSolvent removal

Sources & evidence

ORD record
ord-b1eddc2c175e4b8db43f869d8c9433e6
Source dataset
uspto-grants-2011_08
Patent number
US07999121B2

Reaction notes

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