Catechol → (S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol
Reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S([O:25][CH2:26][C@@H:27]2O[CH2:28]2)(=O)=O)=CC=1>CN(C=O)C>[O:2]1[C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4][CH2:28][C@@H:27]1[CH2:26][OH:25]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
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.
Workup
- temperatureThe reaction was cooled to room temperature
- extractionextracted with diethyl ether (4 times)
- washThe combined organic solution was washed 3 times with 10% potassium carbonate
- customonce with water, once with brine and evaporated in vacuo
- customto yield a white solid which
- customwas purified by flash column chromatography (DCM:Methanol—50:1)
Sources & evidence
- ORD record
- ord-2f9c5c5ddb59488d8122ce9a227f622f
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492431B2
Reaction notes
Loading…