Benzyl Bromide → (2R,3R)-3-(Benzyloxy)butan-2-OL

HRID 2199512Notes

Reaction equation

HRID 2199512 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.[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]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 225936(2R,3R)-ButanediolHCID 23665647Potassium tert-butoxide

Product 1

HCID 12695195(2R,3R)-3-(Benzyloxy)butan-2-OLYield 43%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (2R,3R)-butane-2,3-diol in THF was admixed at room temperature with potassium tert-butylate and the mixture was refluxed for 15 minutes. The mixture was cooled to ca. 50° C. and admixed with benzyl bromide. The mixture was refluxed for 3 hours, then stirred overnight at room temperature. The mixture was diluted with acetic ester and sodium chloride solution and then washed with 1 N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified by means of chromatography (hexane/acetic ester 1:1) (yield: 43%).

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureThe mixture was refluxed for 3 hours
  3. washwashed with 1 N hydrogen chloride solution (1×) and sodium chloride solution (2×)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe residue obtained
  8. customwas purified by means of chromatography (hexane/acetic ester 1:1) (yield: 43%)

Sources & evidence

ORD record
ord-98a84a5307344187b783ff3b22663760
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

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