Water → HCID 66917418, compound

HRID 2355213Notes

Reaction equation

HRID 2355213 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[C:7]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23]C=C)=[C:18]([Br:26])[CH:17]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[O-]S([O-])=O.[Na+].[Na+].O.C[C:35]([OH:38])(C)C.O>CC(O)(C)C.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[C:7]1([S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C@@H:1]([OH:4])[CH2:35][OH:38])=[C:18]([Br:26])[CH:17]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 962WaterHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 58869153HCID 58869153, compoundHCID 714019492-Methylpropan-2-ol--water (1/1)

Product 1

HCID 66917418HCID 66917418, compound

Reagents, catalysts & solvents 2

HCID 178511488HCID 178511488, compoundCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of potassium osmate dihydrate (1.19 mg, 0.0034 mmol), hydroquinidine (anthraquinone-1,4-diyl)diether (7.32 mg, 0.00851 mmol), potassium ferricyanide (843 mg, 2.55 mmol) and K2CO3 (357 mg, 2.55 mmol) in t-BuOH/H2O (3.5 mL/4.5 mL) was cooled to 0° C. and a solution of 4-benzenesulfonyl-2-bromo-1-but-3-enyl-benzene (299 mg, 0.851 mmol) in t-BuOH (1 mL) was added. The reaction was maintained at 0° C. for 18 hours, then Na2SO3 (0.68 g) was added at 0° C. The reaction was allowed to warm to room temperature and water was added. The mixture was extracted twice with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc) to afford (R)-4-(4-benzenesulfonyl-2-bromo-phenyl)-butane-1,2-diol (193 mg) with 86% ee. Chiral column: Chiralpak AS analytical, hexane/isopropanol (75/25), 1.1 mL/min flow rate.

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted twice with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-c9c4a5dc11b145b99e18afa44abca5f1
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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