Benzyl Alcohol → HCID 15065176, compound

HRID 2255156Notes

Reaction equation

HRID 2255156 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:25][CH:26]([CH3:28])[CH3:27])=[N+:11]([O-:24])[C:12](Cl)=[C:13]([CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[CH2:34]([OH:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[H-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[CH2:34]([O:41][C:12]1[C:13]([CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[N:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([CH2:25][CH:26]([CH3:28])[CH3:27])[N+:11]=1[O-:24])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15065175HCID 15065175, compound

Product 1

HCID 15065176HCID 15065176, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolvent

Procedure

There was stirred, for 40 minutes at room temperature, a mixture of 170 mg of 3-benzyloxy-6-chloro-2-isobutyl-5-(2-tetrahydropyranyloxymethyl)pyrazine 1-oxide, 72 mg of tetrabutylammonium bromide, 1.5 ml of dry dimethylformamide, 230 μl of benzyl alcohol and 42.5 mg of 60% sodium hydride. The reaction mixture was stirred at room temperature for 40 minutes, diluted with diethyl ether, then the mixture was washed with water several times and dried over magnesium sulfate. The solvent was removed by evaporation, and the residue was purified by a silica gel thin layer chromatography (developing solvent: 10% by volume of ethyl acetatebenzene) to obtain 136 mg of 2,5-dibenzyloxy-6-isobutyl-3-(2-tetrahydropyranyloxymethyl)pyrazine 1-oxide (Compound B-14) as a colorless oily substance.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 40 minutes
  2. washthe mixture was washed with water several times
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by a silica gel thin layer chromatography (developing solvent: 10% by volume of ethyl acetatebenzene)

Sources & evidence

ORD record
ord-ba5c153f78474f16a2809e002b219abd
Source dataset
uspto-grants-1993_08
Patent number
US05238938

Reaction notes

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