3-(4-Bromophenyl)cyclobutan-1-one → HCID 178521618、化合物

HRID 1988134ノート

反応式

HRID 1988134 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][C:10](=[O:12])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:9][C@H:10]([OH:12])[CH2:11]2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 45896953-(4-Bromophenyl)cyclobutan-1-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 178521618HCID 178521618、化合物収率 100%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a solution of 3-(4-bromo-phenyl)-cyclobutanone (3 g, 13.3 mmol) (J. Med. Chem., 43:721-735(2000)), in anhydrous ether (100 mL) cooled to −20° C. was dropwise added lithium aluminum hydride (1M in THF, 15 mL). The mixture was then allowed to warm to room temperature and stirred for 4 hours. The reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially. After stirring for about 30 minutes, the mixture was filtered through a layer of diatomaceous earth and washed with extra ether (100 mL). The filtrate was evaporated under reduced pressure to provide a colorless oil as the title compound (3.01 g, 100%). 1H NMR (300 MHz, CDCl3) δ 2.0 (m, 2 H), 2.76 (m, 2 H), 2.92 (m, 1 H), 4.28 (m, 1 H), 7.09 (d, J=9 Hz, 2 H), 7.41 (d, J=9 Hz, 2 H); (DCl/NH3) m/z 244 (M+NH4)+.

後処理

  1. customThe reaction was slowly quenched with NaOH (1M, 0.8 mL), H2O (0.8 mL) and NaOH (1M, 0.8 mL) sequentially
  2. stirringAfter stirring for about 30 minutes
  3. filtrationthe mixture was filtered through a layer of diatomaceous earth
  4. washwashed with extra ether (100 mL)
  5. customThe filtrate was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-3544738fa9334258a8a6263fe809a821
出典データセット
uspto-grants-2009_06
特許番号
US07553964B2

反応ノート

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