Sodium Iodide → 1-(2-Cyanoethyl)isochroman

HRID 1417798ノート

反応式

HRID 1417798 の反応式
Cl[CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][O:5]1.[C-]#N.[Na+].[I-].[Na+].[CH3:19][N:20](C=O)C>O>[C:19]([CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][O:5]1)#[N:20]

参加物

6

反応物 4

HCID 5238Sodium Iodide2 回HCID 6228Dimethylformamide2 回HCID 8929Sodium Cyanide2 回HCID 106079661-(2-Chloroethyl)isochroman

生成物 1

HCID 142030711-(2-Cyanoethyl)isochroman

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 1-(2-chloroethyl)isochroman (LXIV, PREPARATION 2, 0.9874 g, 5.02 mmol), sodium cyanide (0.3793 g, 7.74 mmol), sodium iodide (a few mg) and DMF (5 ml) is heated overnight at 856. Additional sodium cyanide (0.5826 g, 11.9 mmol) is then added in two portions, along with DMF (14 ml) and a few mgs of sodium iodide. The mixture is heated at 97° for another two days and then cooled and poured into water. The mixture is extracted several times with ethyl acetate and the combined organic phase is backwashed twice with water, followed by two saline washes, then dried over magnesium sulfate and concentrated to dryness. The crude product is chromatographed on silica gel eluting with ethyl acetate/hexane (10/90). The appropriate fractions are pooled and concentrated to give 1-(2-cyanoethyl)isochroman (LXVI), NMR (CDCl3) 2.11, 2.27-2.72, 2.98, 3.77, 4.13, 4.86 and 7.17 δ.

後処理

  1. temperatureis heated overnight at 856
  2. temperatureThe mixture is heated at 97° for another two days
  3. temperaturecooled
  4. extractionThe mixture is extracted several times with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness
  7. customThe crude product is chromatographed on silica gel eluting with ethyl acetate/hexane (10/90)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-d7fad628c72a4afbaeb72d3f8a753287
出典データセット
uspto-grants-1999_03
特許番号
US05877317

反応ノート

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