Cyanomethylenetributylphosphorane → trans-2,2-dimethyl-5-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanecarbonitrile

HRID 1269957ノート

反応式

HRID 1269957 の反応式
C(C=P(CCCC)(CCCC)CCCC)#N.[OH:17][C@@H:18]1[CH2:23][C@H:22]([C:24]#[N:25])[C:21]([CH3:27])([CH3:26])[CH2:20][CH2:19]1.[CH3:28][C:29]1[C:37](O)=[CH:36][CH:35]=[C:34]2[C:30]=1[CH:31]=[N:32][NH:33]2>C1(C)C=CC=CC=1>[CH3:26][C:21]1([CH3:27])[CH2:20][CH2:19][C@@H:18]([O:17][C:37]2[C:29]([CH3:28])=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][N:32]=[CH:31]3)[CH2:23][C@@H:22]1[C:24]#[N:25]

参加物

5

反応物 3

HCID 4622928CyanomethylenetributylphosphoraneHCID 229335464-methyl-1H-indazol-5-olHCID 45083033cis-5-Hydroxy-2,2-dimethylcyclohexanecarbonitrile

生成物 1

HCID 69429732trans-2,2-dimethyl-5-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanecarbonitrile収率 46%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Under a nitrogen atmosphere, a solution of 90%-cyanomethylenetri-n-butylphosphorane (1.05 g, 4.05 mmol) in toluene (5 ml) was added dropwise to a solution of cis-5-hydroxy-2,2-dimethylcyclohexanecarbonitrile (500 mg, 3.37 mmol) in toluene (12 ml) at room temperature, followed by adding thereto the 4-methyl-1H-indazol-5-ol (507 mg, 3.54 mmol) obtained in Example 402, and the resulting mixture was heated to 100° C. After 4 hours, the reaction solution was concentrated under reduced pressure, and the resulting residue was diluted with chloroform and washed with a 1M-aqueous sodium hydroxide solution. The aqueous layer was re-extracted with chloroform and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain trans-2,2-dimethyl-5-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanecarbonitrile (351.1 mg, 46%).

後処理

  1. additionby adding
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionthe resulting residue was diluted with chloroform
  4. washwashed with a 1M-aqueous sodium hydroxide solution
  5. extractionThe aqueous layer was re-extracted with chloroform
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe organic layer dried
  8. concentrationwas concentrated under reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-8f0bdfd186e1481d9b688535018857ce
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

反応ノート

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