Sodium Hydroxide → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

HRID 1175195Notes

Reaction equation

HRID 1175195 reaction equation
C([O:4][CH2:5][CH:6]1[O:11][C:10]2=[CH:12][S:13][CH:14]=[C:9]2[O:8][CH2:7]1)(=O)C.[OH-].[Na+]>O>[O:8]1[CH2:7][CH:6]([CH2:5][OH:4])[O:11][C:10]2=[CH:12][S:13][CH:14]=[C:9]12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59558874(2,3-Dihydrothieno[3,4-b]-1,4-dioxin-2-yl)methyl acetate

Product 1

HCID 160674382,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 25 mL round bottom flask equipped with a reflux condenser 0.64 g (0.0030 mol) of (2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl acetate was combined with 50% NaOH in water. The reaction was refluxed overnight and then cooled to room temperature. It was then poured into an Erlenmeyer flask filled with 100 mL water. The mixture was acidified then extracted with DCM. The solvent was removed under reduced pressure and column chromatography (7:3 hexanes/ethyl acetate) was performed to give 0.46 g (90%) of product. The structure was confirmed by LC-MS and 1H/13C NMR.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. additionIt was then poured into an Erlenmeyer flask
  3. extractionThe mixture was acidified then extracted with DCM
  4. customThe solvent was removed under reduced pressure and column chromatography (7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-24ebc78300de4948bb996917d5090460
Source dataset
uspto-grants-2010_11
Patent number
US07838688B2

Reaction notes

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