Sodium hydride → HCID 68442724, 화합물

HRID 83180노트

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HRID 83180 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].Cl[C:16]1[N:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][CH:17]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:16]1[N:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 1184246-Chloropyridine-2-carbonitrileHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

생성물 1

HCID 68442724HCID 68442724, 화합물수율 24%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (189 mg, 1.0 mmol) and 6-chloropyridine-2-carbonitrile (150 mg, 1.0 mmol) in toluene (10 mL) was added sodium hydride (55% dispersion in mineral oil, 100 mg, 2.0 mmol) and the mixture heated at 50° C. for 6 h. Then 18-crown-6 (18 mg) was added and the mixture heated at 100° C. overnight. The mixture was then diluted with ethyl acetate and washed with water. The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=7:3) afforded the title compound (70 mg, 24%) as a white solid after trituration with diisopropylether. MS: m/e=292.0 [M+H]+.

후처리

  1. temperaturethe mixture heated at 100° C. overnight
  2. washwashed with water
  3. extractionThe aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=7:3)

출처 및 근거

ORD 기록
ord-403d0da4a5444294bbda05627b91b92c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846719B2

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