Acetone → Methyl 3-bromo-5-(1,2-dihydroxyethyl)benzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=C(C=C)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[N+]1([O-])CC[O:18]CC1.[O-]S([O-])(=S)=O.[Na+].[Na+].[CH3:29][C:30]([CH3:32])=[O:31]>O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:29]([CH:30]([OH:31])[CH2:32][OH:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
7
Procedure
To a stirred solution of methyl 3-bromo-5-vinylbenzoate (1.6 g, 6.6 mmol) and N-methylmorpholine N-oxide (2.0 g, 17.1 mmol) in acetone (40 mL) and water (10 mL) was added dropwise a 5% solution of osmium tetraoxide in water (0.50 g, 0.10 mmol). The reaction mixture was stirred at rt for 3 h, and then a saturated aq. Na2S2O3 solution was added. After being stirred for 30 min, the reaction mixture was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.
Workup
- stirringAfter being stirred for 30 min
- extractionthe reaction mixture was extracted with EtOAc (100 mL×3)
- washThe combined organic layers were washed with water and brine
- customdried
- concentrationconcentrated
- customThe residue was purified by flash column
Sources & evidence
- ORD record
- ord-fae21d0f18f648d9a4efd15ec940dc02
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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