Methanol → HCID 19093474, compound

HRID 487065Notes

Reaction equation

HRID 487065 reaction equation
C([N+](CCC)(CCC)CCC)CC.CO.[OH:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[C:22](=[O:32])[C:23]3[C:28]([C:29]=2[N:30]=1)=[CH:27][CH:26]=[C:25]([Br:31])[CH:24]=3>C(Cl)Cl.C(OCC)(=O)C>[CH:17]([C:18]1[CH:19]=[CH:20][C:21]2[C:22](=[O:32])[C:23]3[C:28]([C:29]=2[N:30]=1)=[CH:27][CH:26]=[C:25]([Br:31])[CH:24]=3)=[O:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 9559TetrapropylammoniumHCID 19093457HCID 19093457, compound

Product 1

HCID 19093474HCID 19093474, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of finely powdered 3 Å molecular sieves, 350 mg (3 mM) of N-methylmorpholine n-oxide, and 70 mg (0.2) of tetrapropylammonium perrhuthenate are added. To a solution of 576 mg (2 mM) of the carbinol, 3-hydroxymethyl-7-bromo-4-aza-9-fluorenone, prepared as described in Example 38, in 20 mL of dry methylene chloride under nitrogen at R.T. the reaction mixture is stirred 15 minutes, diluted with 20 mL of ethyl acetate and filtered through a bed of silica gel, which is washed further with ethyl acetate 5 times. The combined filtrates are concentrated to give the desired aldehyde as yellow solid.

Workup

  1. filtrationfiltered through a bed of silica gel, which
  2. washis washed further with ethyl acetate 5 times
  3. concentrationThe combined filtrates are concentrated

Sources & evidence

ORD record
ord-aa1be7922e2a4969b3fc1fc99ee212d7
Source dataset
uspto-grants-1994_03
Patent number
US05294610

Reaction notes

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