4-Methyloxybenzyl chloride → 1-(4-Methoxy-benzyl)-cyclopropanecarbonitrile

HRID 1010552

반응식

HRID 1010552 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C:18]2([C:21]#[N:22])[CH2:20][CH2:19]2)=[CH:15][CH:14]=1.C1(C#N)CC1.ClCC1C=CC(OC)=CC=1>C1COCC1>[CH3:11][O:12][C:13]1[CH:24]=[CH:23][C:16]([CH2:17][C:18]2([C:21]#[N:22])[CH2:19][CH2:20]2)=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 699934-Methyloxybenzyl chlorideHCID 79637CyclopropanecarbonitrileHCID 866035471-(4-methoxy-benzyl)-cyclopropanecarbonitrile Sodium bis(trimethylsilyl)amide

생성물 1

HCID 574569501-(4-Methoxy-benzyl)-cyclopropanecarbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

1-(4-Methoxy-benzyl)-cyclopropanecarbonitrile Sodium bis(trimethylsilyl)amide (2 M in tetrahydrofuran, 37.5 mL, 75.0 mmol) was slowly added to a solution of cyclopropanecarbonitrile (3.35 g, 49.9 mmol) in THF (30 mL) at room temperature. The reaction mixture was stirred for 20 minutes and then a solution 1-chloromethyl-4-methoxy-benzene (7.83 g, 50.0 mmol) in THF was added. The mixture was heated at reflux for 3 hours and then quenched with a saturated aqueous solution of ammonium chloride (50 mL). The separated aqueous layer was extracted three times with ethyl acetate (50 mL). The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give crude 1-(4-methoxy-benzyl)-cyclopropanecarbonitrile, which was used directly in the next step.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customquenched with a saturated aqueous solution of ammonium chloride (50 mL)
  4. extractionThe separated aqueous layer was extracted three times with ethyl acetate (50 mL)
  5. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-1bd8c24905204990a787022d4ce7456d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977322B2

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