Ethyl Acetate → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 2213698Notes

Reaction equation

HRID 2213698 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][C:7]2=[C:9](C(O)=O)[S:10][C:11](C(O)=O)=[C:6]2[O:5][CH2:4]1.C(OCC)(=O)C>CN(C)C(=O)C.N1C2C(=CC=CC=2)C=CC=1>[O:8]1[CH:3]([CH2:2][OH:1])[CH2:4][O:5][C:6]2=[CH:11][S:10][CH:9]=[C:7]12

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 219583572-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid

Product 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

Reagents, catalysts & solvents 2

HCID 7047QuinolineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst was removed by filtration and the filtrate was washed with acidic water and an aqueous saturated sodium chloride solution. Subsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115–120° C.; 0.05 mm Hg).

Workup

  1. temperatureafter which it was cooled to 25° C
  2. customthe catalyst was removed by filtration
  3. washthe filtrate was washed with acidic water
  4. customSubsequently, the solvent was removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol
  5. customwas isolated by vacuum distillation (115–120° C.; 0.05 mm Hg)

Sources & evidence

ORD record
ord-8821a3b630f34d99a66e56289585e19c
Source dataset
uspto-grants-2006_09
Patent number
US07105620B2

Reaction notes

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