Benzonitrile → HCID 59272919、化合物

HRID 1929751ノート

反応式

HRID 1929751 の反応式
[NH2:1][C@@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6].[C:9](#N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].[Zn+2].[Br-]>[CH3:6][S:5][CH2:4][CH2:3][C@@H:2]1[CH2:7][O:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:1]1

参加物

4

反応物 2

HCID 7505BenzonitrileHCID 7000073D-Methioninol

生成物 1

HCID 59272919HCID 59272919、化合物収率 48.6%

試薬・触媒・溶媒 1

HCID 10421208Zinc bromide触媒

反応条件

温度
120 °C

実験手順

A mixture of (R)-methioninol (4.95 g), benzonitrile (8.3 mL) and zinc bromide (250 mg) was stirred at 120° C. for 90 hours under nitrogen gas atmosphere. After cooling to room temperature, the reaction mixture was filtered and the filtrate was washed with water and a brine, dried over magnesium sulfate and filtered again. The filtrate was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1) to give (R)-4-(2-methylthioethyl)-2-phenyl-4,5-dihydrooxazole (3.94 g, yield: 48.6%) as a colorless oil.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with water
  4. dry with materiala brine, dried over magnesium sulfate
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1)

出典と根拠

ORDレコード
ord-447f02eb0082426faa912d1d62a8f496
出典データセット
uspto-grants-2012_05
特許番号
US08188097B2

反応ノート

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