Benzyl Bromide → (2R,3R)-3-(Benzyloxy)butan-2-OL
Reaction equation
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].CC([O-])(C)C.[K+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.C(OCC)(=O)C.[Cl-].[Na+]>[CH2:13]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
A solution of 4.0 g (44.4 mmol) of (2R,3R)-butane-2,3-diol in 300 ml of THF was admixed at room temperature with 5.0 g (44.6 mmol) of potassium tert-butylate and the mixture was refluxed for 15 minutes. The mixture was cooled to ca. 50° C. and admixed with 5.3 ml (44.6 mmol) of benzyl bromide. The mixture was refluxed for 3 hours, then stirred overnight at room temperature. The mixture was diluted with ethyl acetate and sodium chloride solution and then washed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified chromatographically (hexane/ethyl acetate 1:1). This gave 3.4 g (18.9 mmol; yield: 43%) of the product.
Workup
- temperaturethe mixture was refluxed for 15 minutes
- temperatureThe mixture was refluxed for 3 hours
- washwashed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×)
- dry with materialThe organic phase was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated by evaporation
- customThe resulting residue was purified chromatographically (hexane/ethyl acetate 1:1)
Sources & evidence
- ORD record
- ord-b63ebed23d9b41638a244c19c2363f13
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802686B2
Reaction notes
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