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

HRID 1033008ノート

反応式

HRID 1033008 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6eaf05c58ade4dd4ba95504cf00f458a
出典データセット
uspto-grants-1994_05
特許番号
US05308854

反応ノート

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