Sodium Iodide → 1-(2-Cyanoethyl)isochroman

HRID 1417798노트

반응식

HRID 1417798 반응식
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]

참가 물질

6

반응물 4

HCID 5238Sodium Iodide2회HCID 6228Dimethylformamide2회HCID 8929Sodium Cyanide2회HCID 106079661-(2-Chloroethyl)isochroman

생성물 1

HCID 142030711-(2-Cyanoethyl)isochroman

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d7fad628c72a4afbaeb72d3f8a753287
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877317

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