Ammonium cerous sulfate → HCID 19390019, compound

HRID 1757230Notes

Reaction equation

HRID 1757230 reaction equation
[OH:1][CH:2]1[CH2:14][CH2:13][C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.S([O-])([O-])(=O)=O.[Ce+3].[NH4+].S([O-])([O-])(=O)=O.Br([O-])(=O)=O.[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.O>[OH:12][CH2:11][CH:8]1[CH2:9][CH2:10][C:5]2([CH2:13][CH2:14][C:2](=[O:1])[CH2:3][CH2:4]2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 166930Ammonium cerous sulfateHCID 516892Sodium BicarbonateHCID 19390054HCID 19390054, compoundHCID 23668195Sodium Bromate

Product 1

HCID 19390019HCID 19390019, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

9-Hydroxy-3-hydroxymethyl-spiro[5.5]undecane (0.29 g) and ammonium cerium sulfate (0.830 g) were added to a suspension of sodium bromate (0.230 g ) in acetonitrile and water (9 ml; 70:30). The mixture was heated at 80 ° C. for 3 hrs, cooled to 0 ° C., and treated with sodium bicarbonate to neutral pH. After evaporation under reduced pressure to small volume and extraction with ethyl acetate, the organic layers were dried over anhydrous sodium sulfate and evaporated under reduced pressure to give 0.220 g of a crude residue, that was purified by flash-chromatography (SiO2 ; ethyl acetate/n-hexane 60/40) to give 0.200 g of 9-hydroxymethyl-3-oxo-spiro[5.5]undecane (II-d) a light oil. TLC: Rf=0.35 (SiO2 plates, ethyl acetate/n-hexane 60/40). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 3.50 (2H, d), 2.36 (2H, t), 2.28 (2H, t), 1.85-1.09 (13H, m).

Workup

  1. temperaturecooled to 0 ° C.
  2. customAfter evaporation under reduced pressure
  3. extractionto small volume and extraction with ethyl acetate
  4. dry with materialthe organic layers were dried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customto give 0.220 g of a crude residue, that
  7. customwas purified by flash-chromatography (SiO2 ; ethyl acetate/n-hexane 60/40)

Sources & evidence

ORD record
ord-728f9878d36b43c4bfad05fb74a18d81
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

Loading…