Sodium hydride → HCID 68435388, compound

HRID 1867382Notes

Reaction equation

HRID 1867382 reaction equation
[OH:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C=O)C.C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:1][C:2]2[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Product 1

HCID 68435388HCID 68435388, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.39 g (10 mmol) of the commercial 3-hydroxy-6-methyl-2-pyridinemethanol in 15 ml DMF was cooled (0° C.), treated with 0.52 g (13.00 mmol) of NaH (55% in oil) and after 30 min, with 1.35 mL (10.00 mmol) p-methoxybenzylchlorid. The suspension was stirred 1 h at 0° C. and 2 h at RT. The reaction mixture was diluted with CH2Cl2 and washed with 1M NaOH and brine. The organic layers were dried over magnesium sulfate, evaporated, purified by silica gel column (AcOEt) and crystallized (AcOEt/n-n-heptane) to give 1.55 g (60%) of the title compound as a white solid. MS: 260.0 (MH+).

Workup

  1. washwashed with 1M NaOH and brine
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by silica gel column (AcOEt)
  5. customcrystallized (AcOEt/n-n-heptane)

Sources & evidence

ORD record
ord-886c6b3c817f4e4caa1e757de466d6f9
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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