Dithionite → HCID 59526389, compound

HRID 1967139Notes

Reaction equation

HRID 1967139 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1)C=C.C[N+]1([O-])[CH2:20][CH2:19][O:18]CC1.S(S([O-])=O)([O-])=[O:23].[O-][Si]([O-])=O.[Mg+2]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:13][C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH:19]([OH:18])[CH2:20][OH:23])=[CH:5][CH:6]=1)([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 1086DithioniteHCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 59526205HCID 59526205, compound

Product 1

HCID 59526389HCID 59526389, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a biphasic mixture of 2-(4-allylphenyl)propan-2-ol (5.53 g, 31.4 mmol) and N-Methyl morpholine N-oxide (3.86 g, 32.9 mmol) in acetone (11 mL) and water (22 mL) was added osmium tetroxide (3.14 mL, 0.157 mmol) with vigorous stirring. After 24 hours, dithionite (0.15 g), Florisil (1.5 g), and water (8 mL) were added and allowed to stir for an additional 15 minutes before filtering through a pad of Celite. The filter was rinsed with acetone (2×5 mL, then 2×10 mL), and filtrate was concentrated by rotary evaporation to remove the acetone. The remaining liquid was diluted with 9:1 chloroform:isopropanol (20 mL) and aqueous hydrogen chloride (1 M, 20 mL), the layers were separated, and the acidic (pH=1) aqueous layer was extracted with 9:1 chloroform:isopropanol (2×20 mL). The combined organic layers were washed with 3:1 water:brine (12 mL), saturated aqueous sodium bicarbonate (10 mL), and brine (10 mL). The aqueous layers were combined and saturated with solid sodium chloride (50 cc) by stirring for 90 minutes, and then extracted with 9:1 chloroform:isopropanol (3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated, and the crude material was purified by silica gel chromatography (5-20% methanol/dichloromethane) to afford 3-[4-(1-hydroxy-1-methylethyl)phenyl]propane-1,2-diol as an oil.

Workup

  1. filtrationbefore filtering through a pad of Celite
  2. washThe filter was rinsed with acetone (2×5 mL
  3. concentration2×10 mL), and filtrate was concentrated by rotary evaporation
  4. customto remove the acetone
  5. additionThe remaining liquid was diluted with 9:1 chloroform
  6. customisopropanol (20 mL) and aqueous hydrogen chloride (1 M, 20 mL), the layers were separated
  7. extractionthe acidic (pH=1) aqueous layer was extracted with 9:1 chloroform
  8. washThe combined organic layers were washed with 3:1 water
  9. stirringby stirring for 90 minutes
  10. extractionextracted with 9:1 chloroform
  11. dry with materialThe combined organic extracts were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customthe crude material was purified by silica gel chromatography (5-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-3ed98df09a694fbb819f5ba771ee2d01
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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