Methanol → HCID 15065177, compound

HRID 2255157Notes

Reaction equation

HRID 2255157 reaction equation
CO.[H-].[Na+].CN(C)C=O.[CH2:10]([O:17][C:18]1[C:23]([CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)=[N:22][C:21]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:20]([CH2:40][CH:41]([CH3:43])[CH3:42])[N+:19]=1[O-:44])C1C=CC=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[CH2:33]([O:32][C:21]1[C:20]([CH2:40][CH:41]([CH3:43])[CH3:42])=[N+:19]([O-:44])[C:18]([O:17][CH3:10])=[C:23]([CH2:24][O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[N:22]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15065176HCID 15065176, compound

Product 1

HCID 15065177HCID 15065177, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

There was stirred, for 1 hour at room temperature, a mixture of 55 μl of methanol, 11 mg of 60% sodium hydride, 22 mg of tetra-n-butylammonium bromide, 50 μl of dimethylformamide and 65 mg of 2,5-dibenzyloxy-6-isobutyl-3-(2-tetrahydropyranyloxymethyl)pyrazine 1-oxide (Compound B-14). The reaction mixture was mixed with diethyl ether. The mixture was washed with water several times and dried with magnesium sulfate, then the solvent was removed by evaporation. The residue was purified by silica gel thin layer chromatography (developing solvent: 30 volume % ethyl acetate-n-hexane) to obtain 50 mg of 3-benzyloxy-2-isobutyl-6-methoxy-5-(2-tetrahydropyranyloxymethyl)pyrazine 1-oxide (Compound B-15) as a colorless oily substance.

Workup

  1. washThe mixture was washed with water several times
  2. dry with materialdried with magnesium sulfate
  3. customthe solvent was removed by evaporation
  4. customThe residue was purified by silica gel thin layer chromatography (developing solvent: 30 volume % ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-837c54dc4bdb4726ac0ba3cef3498f64
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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