Water → {4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile

HRID 1263520노트

반응식

HRID 1263520 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][O:26][CH3:27])[CH:21]=[CH:20][C:19]=1[CH:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.O>COCCOC.C(OCC)C>[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH2:25][O:26][CH3:27])[CH:21]=[CH:20][C:19]=1[CH:28]1[CH2:33][CH2:32][C:31](=[CH:5][C:3]#[N:4])[CH2:30][CH2:29]1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 121351704-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

생성물 1

HCID 22337767{4-[2,4-Bis(methoxymethoxy)phenyl]cyclohexylidene}acetonitrile수율 66%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

To a round bottomed flask equipped was added sodium hydride (40 mg, 60% dispersion in mineral oil) and 1, 2-dimethoxyethane (10 ml). Diethyl cyanomethylphosphonate (102 μl, 0.95 mmol) was added and the reaction mixture allowed to warm to room temperature. 4-[(2,4-Bis(methoxymethoxy)phenyl)]cyclohexanone (200 mg) was added as a solution in 1,2-dimethoxyethane (10 ml) and the reaction mixture stirred for 17 hr at room temperature. The reaction mixture was poured into a separating funnel containing water (50 ml) and diethyl ether (50 ml). The layers were separated and the aqueous phase extracted with diethyl ether (2×20 ml). The combined organic layers were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo, to give an oil. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:2, v/v) afforded the title compound (141 mg, 66%) as a pale yellow oil. δH (CD3OD) 1.57-1.70 (2H, m), 2.02-2.25 (2H, m), 2.34-2.49 (2H, m), 2.60 (1H, m), 3.03 (1H, m), 3.24 (1H, m), 3.47 (3H, s), 3.52 (3H, s), 5.17 (2H, s), 5.23(2H, s), 5.33 (1H, s), 6.68 (1H, dd), 6.83 (1H, d), 7.09 (1H, d).

후처리

  1. customTo a round bottomed flask equipped
  2. additionThe reaction mixture was poured into a separating funnel
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with diethyl ether (2×20 ml)
  5. washThe combined organic layers were washed with brine (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an oil
  10. customPurification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:2, v/v)

출처 및 근거

ORD 기록
ord-d8463195f3334732ab7896241ca64591
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541473B2

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