HCID 19361724, compound → HCID 178504272, compound

HRID 376282Notes

Reaction equation

HRID 376282 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:10]=1)C1C=CC=CC=1.[H][H]>[Ni].C(O)C>[CH3:22][Si:21]([CH3:24])([CH3:23])[CH2:20][CH2:19][O:18][CH2:17][O:16][CH2:15][C:11]1[N:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 19361724HCID 19361724, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178504272HCID 178504272, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

7 g of Raney Nickel are added to a solution of 7 g of 2-benzyloxy-6-(2-trimethylsilanyl-ethoxymethoxy-methyl)pyridine in 75 ml of ethanol saturated with hydrogen. The suspension is stirred vigorously under a low hydrogen pressure at room temperature for 1 hour 30 minutes. The solid in suspension is removed by filtration on celite and then the ethanol is evaporated off. The title product is isolated by chromatography on a silica column (eluent: dichloromethane/methanol; 98:2). 4 g of a colorless oil are recovered.

Workup

  1. customThe solid in suspension is removed by filtration on celite
  2. customthe ethanol is evaporated off

Sources & evidence

ORD record
ord-63c77534104a457c963045dc44bf5fbc
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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