MAGNESIUM SILICATE (synthetic) → HCID 21864726, compound

HRID 2187577Notes

Reaction equation

HRID 2187577 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[CH2:12][CH:7]2C=C1.C[N+]1([O-])[CH2:19][CH2:18][O:17]CC1.[O-:21][Si]([O-])=O.[Mg+2].OS([O-])=O.[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]1[CH2:12][CH:7]2[CH:19]([OH:21])[CH:18]1[OH:17]

Participants

8

Reactant 4

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 82029Methyl morpholine oxideHCID 1440165-Iodo-1,4-dihydro-1,4-methanonaphthaleneHCID 23665763Sodium Bisulfite

Product 1

HCID 21864726HCID 21864726, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

5-Iodo-1,4-dihydro-1,4-methano-naphthalene (20 g) and N-methyl morpholine N-oxide (17.61 g, 130 mmol) were stirred in acetone (90 mL) and H2O (13 mL). To this was added a solution of OsO4 (0.2 mL, 2.5% wt, solution in t-BuOH, 0.02 mmol). After 144 hours, florisil (5 g) and saturated aqueous NaHSO3 solution (3 mL) were added and stirred for ½ hour. The mixture was filtered through a Celite pad and the filtrate concentrated to produce an oil which was purified by chromatography on Silica gel eluting with a gradient of hexanes to 100% EtOAc to provide a yellow solid (13.73 g). APCl MS m/e 301.1 [(M−1)+].

Workup

  1. filtrationThe mixture was filtered through a Celite pad
  2. concentrationthe filtrate concentrated
  3. customto produce an oil which
  4. customwas purified by chromatography on Silica gel eluting with a gradient of hexanes to 100% EtOAc

Sources & evidence

ORD record
ord-570c7f66f1404e1abb710ddbbdc974e0
Source dataset
uspto-grants-2002_06
Patent number
US06410550B1

Reaction notes

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