Bis(2-chloroethyl) ether → 4-(3-Methoxyphenyl)oxane-4-carbonitrile

HRID 272808

반응식

HRID 272808 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:10]#[N:11])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 88310(3-Methoxyphenyl)acetonitrile

생성물 1

HCID 187863664-(3-Methoxyphenyl)oxane-4-carbonitrile수율 28%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

3-Methoxyphenylacetonitrile (10 g, 67.9 mmol) in DMF (50 ml) was added slowly to a suspension of NaH (5.04 g, 150 mmol) in DMF (50 ml) at 0° C. under N2. The reaction was allowed to warm to room temperature and stirred for 30 nms. The reaction was cooled to 0° C. and bis(2-chloroethyl)ether (10.7 g, 74.7 mmol) in DMF (100 ml) was added dropwise over 80 min. The reaction was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with water (500 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were washed with brine (3×50 ml), dried over MgSO4, filtered, washed with ethyl acetate and concentrated in vacuo. The crude mixture was purified by column chromatography, eluting with heptane increasing the polarity to heptane:ethyl acetate (90:10), to give 4-(3-methoxyphenyl)tetrahydro-pyran-4-carbonitrile (4.1 g, 28%).

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 hour
  4. customThe reaction was quenched with water (500 ml)
  5. extractionextracted with ethyl acetate (3×100 ml)
  6. washThe combined organic extracts were washed with brine (3×50 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. washwashed with ethyl acetate
  10. concentrationconcentrated in vacuo
  11. customThe crude mixture was purified by column chromatography
  12. washeluting with heptane increasing the polarity to heptane:ethyl acetate (90:10)

출처 및 근거

ORD 기록
ord-c0296a5b2e614158a90ed9b8370dbd3d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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