3-(4-Bromophenyl)cyclobutan-1-one → HCID 178521618, 화합물

HRID 1988134노트

반응식

HRID 1988134 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 178521618HCID 178521618, 화합물수율 100%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3544738fa9334258a8a6263fe809a821
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07553964B2

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