Hydrochloric Acid → 4-Cyclopentyl-3-(trifluoromethyl)benzonitrile

HRID 217471

反応式

HRID 217471 の反応式
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].CN1CCCC1=O.[CH:21]1([Mg]Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.Cl>C1COCC1.C(OCC)C.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Fe]>[CH:21]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 27364744-Chloro-3-(trifluoromethyl)benzonitrileHCID 178419650HCID 178419650、化合物

生成物 1

HCID 592144344-Cyclopentyl-3-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 3

HCID 11110968Iron (III) acetylacetonate触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-chloro-3-(trifluoromethyl)benzonitrile (1.5 g), iron (III) acetylacetonate (130 mg), and 1-methylpyrrolidin-2-one (4 mL) in THF (45 mL) was added a 1 M solution of cyclopentyl magnesium bromide in THF (8.8 mL) at 5° C., followed by stirring at room temperature for 0.5 hours and diluting with diethylether. 1 M hydrochloric acid was slowly added thereto, followed by extraction with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5) to obtain 4-cyclopentyl-3-(trifluoromethyl)benzonitrile (367 mg) as a white solid.

後処理

  1. extractionfollowed by extraction with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=100:0 to 95:5)

出典と根拠

ORDレコード
ord-35b866f798f740aebaad3a0c86cb4316
出典データセット
uspto-grants-2012_06
特許番号
US08193378B2

関連ノート

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