Hydrochloric Acid → HCID 17861363、化合物

HRID 1294160ノート

反応式

HRID 1294160 の反応式
O1CC[CH2:3][CH2:2]1.[H-].[Na+].[CH3:8][O:9][CH2:10][O:11][CH2:12][C:13]1[N:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][C:17]=1[CH:18]=O.Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.CS(C)=O.O>[CH3:8][O:9][CH2:10][O:11][CH2:12][C:13]1[N:14]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:16][C:17]=1[CH2:18][CH2:2][CH3:3]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 114592744-[(Methoxymethoxy)methyl]-2-phenyl-1,3-oxazole-5-carbaldehyde

生成物 1

HCID 17861363HCID 17861363、化合物収率 36%

試薬・触媒・溶媒 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 679Dimethyl Sulfoxide溶媒2 回HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a mixture of dimethyl sulfoxide (80 mL) and tetrahydrofuran (200 mL) was added sodium hydride (6.0%, oil, 1.81 g) at room temperature and the mixture was stirred at 50° C. for 1.5 hrs. After allowing the reaction mixture to cool to room temperature, ethyl triphenylphosphonium bromide (13.66 g) was added and the mixture was stirred at room temperature for 30 min. A solution (20 mL) of 4-methoxymethoxymethyl-2-phenyl-5-oxazolecarbaldehyde (7.0 g) in dimethyl sulfoxide was added to the reaction mixture and the mixture was heated under reflux for 1 hr. Water was added to the reaction mixture, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:6, v/v). A mixture of the obtained oil, 5% palladium carbon (2.0 g) and tetrahydrofuran (200 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure to give 4-methoxymethoxymethyl-2-phenyl-5-propyloxazole as a colorless oil (2.65 g, 36%).

後処理

  1. temperatureto cool to room temperature
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give an oil from a fraction
  10. washeluted with ethyl acetate-hexane (1:6, v/v)
  11. additionA mixture of the obtained oil, 5% palladium carbon (2.0 g) and tetrahydrofuran (200 mL)
  12. customwas subjected to catalytic hydrogenation at room temperature
  13. filtrationAfter filtering off the catalyst
  14. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-cf1b1b9ea61d45278889eebaeed7294e
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

反応ノート

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