Dimethylformamide → 3-Isopropylbenzofuran-2-carbaldehyde

HRID 2097147노트

반응식

HRID 2097147 반응식
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH:5]=1)([CH3:3])[CH3:2].[Li]CCCC.CN([CH:21]=[O:22])C>C1COCC1>[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH:21]=[O:22])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 112174123-IsopropylbenzofuranHCID 178418339Butyllithium

생성물 1

HCID 577420813-Isopropylbenzofuran-2-carbaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (0° C.) solution of 3-isopropylbenzofuran (250 mg, 1.56 mmol) in THF (1 mL) is added nBuLi (2 mL, 2 mmol) drop wise and the reaction is stirred for 30 minutes. DMF (1 mL) was added to the reaction and stirred at room temperature overnight. The solution is placed in an ice bath and carefully quenched with 5% aqueous 110 solution (2 mL), and extracted with ethyl acetate (3×5 mL), dried over sodium sulfate and concentrated. The product was purified on silica with 100% hexanes to yield title compound in as a colorless oil (250 mg, 85%): 1H NMR (400 MHz, CDCl3) δ 10.10 (s, 1H), 7.78 (d, 1H, J=9.0 Hz), 7.55 (d, 1H, J=9.0 Hz), 7.32-7.24 (m, 2H), 3.11-3.07 (m, 1H), 1.33-1.31 (2s, 6H).

후처리

  1. stirringstirred at room temperature overnight
  2. customThe solution is placed in an ice bath
  3. customcarefully quenched with 5% aqueous 110 solution (2 mL)
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified on silica with 100% hexanes

출처 및 근거

ORD 기록
ord-ef972312a3b143e0b05b5dfb8919dfbb
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

반응 노트

불러오는 중…