Acetonitrile → 2,3-Dihydro-1H-indene-2-carbonitrile

HRID 450727

反応式

HRID 450727 の反応式
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1OS(C)(=O)=O.[C:15](#[N:17])C>[C-]#N.C([N+](CC)(CC)CC)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:15]#[N:17]

参加物

4

反応物 2

HCID 6342AcetonitrileHCID 2552212,3-Dihydro-1h-inden-2-yl methanesulfonate

生成物 1

HCID 232396182,3-Dihydro-1H-indene-2-carbonitrile収率 52%

試薬・触媒・溶媒 1

HCID 3014735Tetraethylammonium cyanide触媒

反応条件

温度
55 °C

実験手順

A mixture of methanesulfonic acid indan-2-yl ester (18.65 g, 87.9 mmol) and tetraethylammonium cyanide (15.10 g) in acetonitrile (180 mL) was heated to 55° C. for 5 hours, cooled and concentrated. The residue was partitioned between ethyl acetate and water, and the organic phase separated. This was dried over MgSO4 and the filtered solution was concentrated and then separated by column chromatography (dichloromethane:ethyl acetate, 6:1-1:1) to give the product as a red solid (6.51 g, 52%).

後処理

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organic phase separated
  5. dry with materialThis was dried over MgSO4
  6. concentrationthe filtered solution was concentrated
  7. customseparated by column chromatography (dichloromethane:ethyl acetate, 6:1-1:1)

出典と根拠

ORDレコード
ord-b09be4f86e70459ba16dd2d42dc4a312
出典データセット
uspto-grants-2013_07
特許番号
US08486984B2

関連ノート

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