Dimethylformamide → Methyl 4-(5-formylthiophen-2-yl)butanoate

HRID 874988

反応式

HRID 874988 の反応式
O=P(Cl)(Cl)Cl.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].CN([CH:21]=[O:22])C>>[CH:21]([C:10]1[S:6][C:7]([CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:9]=1)=[O:22]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 1407664-(2-Thienyl)butanoic acid methyl ester

生成物 1

HCID 53861603Methyl 4-(5-formylthiophen-2-yl)butanoate収率 83%

反応条件

温度
110 °C

実験手順

Freshly distilled POCl3 (0.4 MI, 4.12 mmol) was added to a solution of methyl 4-(thiophen-2-yl)butanoate (1.1 g, 5.97 mmol) in dry DMF (0.7 MI) at 0° C. The reaction mixture was further heated to 110° C. for 1.5 h, then cooled to room temperature and quenched with ice water. The Ph of the reaction mixture was adjusted to ˜7 using aqueous Na2CO3 solution. The organic product was extracted with diethyl ether and the combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to get methyl 4-(5-formylthiophen-2-yl)butanoate (1.0 g, yield 83%), which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 9.82 (s, 1H), 7.63-7.61 (d, J=3.7 Hz, 1H), 6.94-6.92 (m, 1H), 3.68 (s, 3H), 2.96-2.91 (t, J=7.5 Hz, 2H), 2.42-2.37 (m, 2H), 2.09-1.99 (m, 2H). MS (ESI) m/z: Calculated for C10H12O3S: 212.05. found: 212.9 (M+H)+

後処理

  1. temperaturecooled to room temperature
  2. customquenched with ice water
  3. extractionThe organic product was extracted with diethyl ether
  4. washthe combined extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-99909b34a1474435855dd16a9d717088
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

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