Hydrogen Peroxide → (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol

HRID 133800Notes

Reaction equation

HRID 133800 reaction equation
B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[C:23]1([CH2:29][C:30]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+].OO>C(OCC)C.O>[C:23]1([CH2:29][C@H:30]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[OH:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 109980962-Phenyl-1-(thiazol-2-yl)ethanoneHCID 91873398(+)-b-Chlorodiisopinocamphenylborane

Product 1

HCID 11084983(1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanolYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Following the method of Itako et al. (Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 48(35), 1992, 7251-7264), to a 0° C. (ice-water bath) solution of (+)-B-chlorodiisopinocamphenylborane (+-DIP-Chloride, 3.9 g, 12 mmol) in diethyl ether (3 mL) is added dropwise a solution of 2-phenyl-1-(1,3-thiazol-2-yl)ethanone (0.83 g, 4.1 mmol, from Reference Example 2) in diethyl ether (17 mL). The mixture is stirred for 6 hours at 0° C. and then is allowed to sit in a −5° C. freezer overnight. The next day, 10% aqueous sodium hydroxide solution (10 mL) is added at 0° C. with stirring. Aqueous hydrogen peroxide solution (30%, 1.5 mL) is then added and the mixture is allowed to stir at room temperature for 2 hours. The biphasic mixture is diluted with water (50 mL). The two layers are partitioned and the aqueous phase is saturated with potassium carbonate and then extracted thrice with diethyl ether. The combined extracts are washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a bright golden oil, which is purified by flash chromatography (silica gel, hexanes/ethyl acetate). A light yellow solid (0.60 g, 72%) is provided. MS (ES+): (M+H)=206.0

Workup

  1. waitto sit in a −5° C. freezer overnight
  2. stirringwith stirring
  3. stirringto stir at room temperature for 2 hours
  4. customThe two layers are partitioned
  5. extractionextracted thrice with diethyl ether
  6. washThe combined extracts are washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a bright golden oil, which
  10. customis purified by flash chromatography (silica gel, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-caa7a33c8db34972a025f6730bc06216
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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