Potassium Acetate → (2,3-Dihydrothieno[3,4-b]-1,4-dioxin-2-yl)methyl acetate

HRID 1175194Notes

Reaction equation

HRID 1175194 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2=[CH:9][S:10][CH:11]=[C:6]2[O:5][CH2:4]1.[C:12]([O-:15])(=[O:14])[CH3:13].[K+]>CS(C)=O>[C:12]([O:15][CH2:2][CH:3]1[O:8][C:7]2=[CH:9][S:10][CH:11]=[C:6]2[O:5][CH2:4]1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 569236862-(Bromomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine

Product 1

HCID 59558874(2,3-Dihydrothieno[3,4-b]-1,4-dioxin-2-yl)methyl acetateYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 50 mL Schlenk tube 1.00 g of to 2-(bromomethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine was combined with 0.5 g (0.0051 mol) potassium acetate and 25 mL DMSO. The tube was sealed and stirred for 1 h at 100 C. At this time TLC indicated complete consumption of starting material. The reaction was poured into water and extracted with ether. After removing the ether under reduced pressure column chromatography was performed using 90% methylene chloride in hexane to isolate a light yellow oil in 90% yield. The structure and purity were confirmed by 1H/13C NMR and GC-MS.

Workup

  1. customThe tube was sealed
  2. customconsumption of starting material
  3. additionThe reaction was poured into water
  4. extractionextracted with ether
  5. customAfter removing the ether under reduced pressure column chromatography
  6. customto isolate a light yellow oil in 90% yield

Sources & evidence

ORD record
ord-bff1d313d43f4143960cbb83b4029bc5
Source dataset
uspto-grants-2010_11
Patent number
US07838688B2

Reaction notes

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