Acetonitrile → 3-(Naphthalen-1-yl)-3-oxopropanenitrile

HRID 928242ノート

反応式

HRID 928242 の反応式
C([Li])CCC.CCCCCC.[C:12](#[N:14])[CH3:13].[C:15]1([C:25](OCC)=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>O1CCCC1>[C:15]1([C:25]([CH2:13][C:12]#[N:14])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 8058HexaneHCID 76364Ethyl 1-naphthoateHCID 178418339Butyllithium

生成物 1

HCID 219434673-(Naphthalen-1-yl)-3-oxopropanenitrile収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2.50 M of n-butyllithium in hexane (49.9 mL, 125 mmol) in tetrahydrofuran (49.9 mL) cooled to −78° C. is added acetonitrile (6.52 mL, 125 mmol) drop-wise. The resulting cloudy mixture is stirred for 30 min. Ethyl α-napthoate (8.87 mL, 49.9 mmol) is added drop-wise and the reaction mixture is stirred at −78° C. for 2 hr. The reaction is warmed to room temperature, quenched with acetic acid (50 ml) and partitioned between ethyl acetate and water. The organic layer is dried over Na2SO4, filtered and concentrated in vacuo. The crude material is purified by column chromatography (eluent: 5-15% CH2Cl2/methanol) to provide 1-naphthoylacetonitrile (6.99 g, yield 72%). 1H NMR (400 MHz, CDCl3) δ 8.82 (d, J=8.7 Hz, 1H), 8.11 (d, J=8.3 Hz, 1H), 7.90 (t, J=8.1 Hz, 2H), 7.71-7.64 (m, 1H), 7.57 (dt, J=15.5, 7.2 Hz, 2H), 4.21 (s, 2H).

後処理

  1. stirringthe reaction mixture is stirred at −78° C. for 2 hr
  2. customquenched with acetic acid (50 ml)
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material is purified by column chromatography (eluent: 5-15% CH2Cl2/methanol)

出典と根拠

ORDレコード
ord-7a0ccae401454707b989490608e1fc1f
出典データセット
uspto-grants-2016_03
特許番号
US09290500B2

反応ノート

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