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

HRID 1033008노트

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HRID 1033008 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6eaf05c58ade4dd4ba95504cf00f458a
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05308854

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