Acetone → HCID 54010919, compound

HRID 2295288Notes

Reaction equation

HRID 2295288 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]1C2CC[CH:11]([CH:12]=[CH:13]2)[S:10]1.C[N+]1([O-])CC[O:21]CC1.[CH3:25][C:26]([CH3:28])=[O:27]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]1[CH:28]2[CH2:13][CH2:12][CH:11]([CH:25]([OH:21])[CH:26]2[OH:27])[S:10]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 54008977HCID 54008977, compound

Product 1

HCID 54010919HCID 54010919, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

A mixture of 8 g (0.033 m) of the product of Example 8, 5.3 g (0.039 m) of N-methylmorpholine N-oxide, 4 ml of 2.5% osmium tetroxide in t-butanol, and 20 ml of acetone was stirred for four hours then extracted with ethylacetate. The organic solution was washed with brine, dried, and stripped to give 12 g of crude product which was purified by dry column chromatography (silica gel, ethylacetate:hexane::1:1) to yield 5.8 g of the title compound as a white solid, M. 124°-6° C.

Workup

  1. extractionthen extracted with ethylacetate
  2. washThe organic solution was washed with brine
  3. customdried
  4. customto give 12 g of crude product which
  5. customwas purified
  6. dry with materialby dry column chromatography (silica gel, ethylacetate:hexane::1:1)

Sources & evidence

ORD record
ord-1fce2b9c6fcf44359d3cd9b5b970d7bc
Source dataset
uspto-grants-1984_01
Patent number
US04424213

Reaction notes

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