Sodium hydride → 3-[(Benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine

HRID 1033008Notes

Reaction equation

HRID 1033008 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]([OH:11])=[CH:9][C:8]([CH2:12][CH3:13])=[C:7]([CH3:14])[N:6]=1.Cl[CH2:16][C:17]1[O:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1>CN(C)C=O.C(OCC)C>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[CH2:16][O:11][C:10]1[C:5]([O:4][CH3:3])=[N:6][C:7]([CH3:14])=[C:8]([CH2:12][CH3:13])[CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 20619892-(Chloromethyl)-1,3-benzoxazoleHCID 118194042-Methoxy-3-hydroxy-5-ethyl-6-methylpyridine

Product 1

HCID 103348493-[(Benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridineYield 33.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A quantity of 60% sodium hydride in mineral oil (24 mg, 0.6 mmol) was added to a solution of 2-methoxy-3-hydroxy-5-ethyl-6-methylpyridine (77 mg, 0.46 mmol) in dry dimethylformamide (2 mL). After gas evolution ceased, 2-(chloromethyl) benzoxazole (100 mg, 0.6 mmol) was added and the reaction mixture warmed at 60° C. for one hour. The reaction was then cooled, diluted with diethyl ether, the ether extract washed with water, dried (Na2SO4), filtered and evaporated to give 151 mg of crude mixture. This mixture was flash chromatographed on silica gel, eluting with 0.5% methanol/chloroform. Combined appropriate fractions gave 46 mg (32%) of oily product.

Workup

  1. temperatureThe reaction was then cooled
  2. extractionthe ether extract
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give 151 mg of crude mixture
  8. customchromatographed on silica gel
  9. washeluting with 0.5% methanol/chloroform

Sources & evidence

ORD record
ord-6eaf05c58ade4dd4ba95504cf00f458a
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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