Water → Ethyl 3-(4-(methoxymethoxy)phenyl)propiolate

HRID 884060

반응식

HRID 884060 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[C:13]#[CH:14].O>CN(C=O)C.[Cu-]=O>[CH3:11][O:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][CH:4]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 12182Ethyl propiolateHCID 110327301-Iodo-4-(methoxymethoxy)benzene

생성물 1

HCID 57693052Ethyl 3-(4-(methoxymethoxy)phenyl)propiolate수율 52%

시약·촉매·용매 2

HCID 178419072HCID 178419072, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

Under an Ar atmosphere, a mixture of 1-iodo-4-(methoxymethoxy)benzene (500 mg, 1.89 mmol), Ethyl propiolate (371 mg, 3.78 mmol) and Copper(I) oxide (270 mg, 1.89 mmol) in DMF (10 ml) was heated at 110° C. for 16 h. After cooling, H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with H2O, brine, dried over Na2SO4, then concentrated. Purification by silica gel flash column chromatography (eluent: hexane/AcOEt, 15:1) gave 2e (52%). 2e: colorless oil; 1H-NMR (CDCl3) δ 1.36 (3H, t, J=7.1), 3.48 (3H, 2), 4.29 (2H, q, J=7.1), 5.20 (2H, s), 7.02 (2H, d, J=8.8 Hz), 7.54 (2H, d, J=8.8 Hz).

후처리

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with AcOEt
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel flash column chromatography (eluent: hexane/AcOEt, 15:1)

출처 및 근거

ORD 기록
ord-9cfb2d551c5f45b49a43cd506448d58f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236987B2

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