Ammonium Chloride → cis-5-Hydroxy-2,2-dimethylcyclohexanecarbonitrile

HRID 1269956ノート

反応式

HRID 1269956 の反応式
[CH3:1][C:2]1([CH3:11])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH:3]1[C:9]#[N:10].[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:8][C@@H:5]1[CH2:4][C@H:3]([C:9]#[N:10])[C:2]([CH3:11])([CH3:1])[CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2 回HCID 229338622,2-Dimethyl-5-oxocyclohexane-1-carbonitrile

生成物 1

HCID 45083033cis-5-Hydroxy-2,2-dimethylcyclohexanecarbonitrile収率 75.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Under a nitrogen atmosphere, a solution of 2,2-dimethyl-5-oxocyclohexanecarbonitrile (4.0 g, 0.0265 mol) in methanol (30 ml) was added dropwise to a solution of sodium borohydride (1.00 g, 0.0265 mol) in methanol (40 ml) at 0° C. After 1 hour, sodium borohydride (0.0133 mol) was further added thereto and the resulting mixture was warmed up to room temperature. After 45 minutes, a saturated aqueous ammonium chloride solution was added to the reaction solution and then the methanol was concentrated under reduced pressure. The resulting aqueous solution was diluted with water and extracted with chloroform, and 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 cis-5-hydroxy-2,2-dimethylcyclohexanecarbonitrile (3.0550 g, 75%).

後処理

  1. waitAfter 45 minutes
  2. concentrationthe methanol was concentrated under reduced pressure
  3. additionThe resulting aqueous solution was diluted with water
  4. extractionextracted with chloroform
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe organic layer dried
  7. concentrationwas concentrated under reduced pressure
  8. 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-9cd9849522a14908be0f27415ac4f6ba
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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