Trimethylsilyldiazomethane → [5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol

HRID 1964954Notes

Reaction equation

HRID 1964954 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9](=[O:16])[CH:10]=[C:11]([CH2:14][OH:15])[NH:12][CH:13]=2)=[CH:4][CH:3]=1.[CH3:19][Si](C=[N+]=[N-])(C)C>CO.CN(C)C=O.CCCCCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][O:7][C:8]2[C:9]([O:16][CH3:19])=[CH:10][C:11]([CH2:14][OH:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 580875645-(4-chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one

Product 1

HCID 58087092[5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent2×

Procedure

5-(4-Chloro-benzyloxy)-2-hydroxymethyl-1H-pyridin-4-one (639, 1.06 g, 3.99 mmol) was dissolved in methanol (8.5 mL) and N,N-dimethylformamide (46 mL). Trimethylsilyldiazomethane in hexane (2.00 M, 3.99 mL) was added. The reaction was stirred at room temperature overnight, then additional trimethylsilyldiazomethane in hexane (2.00 M, 3.99 mL) was added. The reaction was stirred at room temperature for 2 days. The mixture was adsorbed onto silica and purified by silica gel chromatography, methanol:dichloromethane to provide the compound (640, 798 mg, 72%). MS(ESI) [M+H+]+=280.4, 282.4.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 days
  2. custompurified by silica gel chromatography, methanol
  3. customdichloromethane to provide the compound (640, 798 mg, 72%)

Sources & evidence

ORD record
ord-7ed45766e82741c88dd955d1b01c125d
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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