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

HRID 884060ノート

反応式

HRID 884060 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9cfb2d551c5f45b49a43cd506448d58f
出典データセット
uspto-grants-2012_08
特許番号
US08236987B2

反応ノート

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