Reaction #1106683

Reaction equation

Catechol

potassium carbonate

(2R)-glycidyl tosylate

→

((2S)-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol

Solvents

DMF

—

ice water

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled to room temperature
2. 2
   Extractionextracted with diethyl ether (4 times)
3. 3
   WashThe combined organic solution was washed 3 times with 10% potassium carbonate
4. 4
   Otheronce with water, once with brine and evaporated in vacuo
5. 5
   Otherto yield a white solid which
6. 6
   Otherwas purified by flash column chromatography (DCM:Methanol—50:1)

Procedure

Catechol (13.2 g, 0.12 mol) and potassium carbonate (16.6 g, 0.12 mol) were stirred in DMF (250 mL) and (2R)-glycidyl tosylate (22.8 g, 0.10 mol) was added and the reaction was stirred at 60° C. for 24 h. The reaction was cooled to room temperature and diluted with ice water (1 L) and extracted with diethyl ether (4 times). The combined organic solution was washed 3 times with 10% potassium carbonate, once with water, once with brine and evaporated in vacuo to yield a white solid which was purified by flash column chromatography (DCM:Methanol—50:1) to yield ((2S)-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol as a solid.

Source