Cesium carbonate → 3-(Dihydro-2-furanyl)benzaldehyde

HRID 10747

반응식

HRID 10747 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[O:10]1[CH:14]=[CH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:10]1[CH:11]=[CH:12][CH2:13][CH:14]1[C:2]1[CH:9]=[C:6]([CH:5]=[CH:4][CH:3]=1)[CH:7]=[O:8]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 709342,3-DihydrofuranHCID 765833-Bromobenzaldehyde

생성물 1

HCID 219810903-(Dihydro-2-furanyl)benzaldehyde수율 40%

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
45 °C

실험 절차

Ex-119A: 5-Bromobenzaldehyde (0.5 g, 2.7 mmol) and 2,3-dihydrofuran (0.56 g, 8.1 mmol) were dissolved in dioxane (5.0 mL). Nitrogen was bubbled into the solution for 15 min followed by the sequential addition of cesium carbonate (0.96 g, 2.9 mmol) and bis(tri-t-butylphosphine)palladium(0) (0.014 g, 0.027 mmol). The solution was immediately heated to 45° C. and aged for 24 h. Upon completion, as determined by HPLC, the reaction was diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over sodium sulfate and concentrated to a brown oil. Silica gel chromatography (ethyl acetate/hexanes, 1:9) gave 0.18 g (40%) of 3-(2,3-dihydro-furan-2-yl)-benzaldehyde as a clear, colorless oil. 1H-NMR (300 MHz, CDCl3) δ 10.03 (s, 1H), 7.88 (s, 1H), 7.82 (d, 1H, J=7.2 Hz), 7.62–7.64 (m, 1H), 7.53 (t, 1H, J=7.2 Hz), 6.48 (q, 1H, J=Hz), 5.60 (dd, 1H, J=8.1, 10.8 Hz), 4.98 (q, 1H, J=3.3 Hz), 3.15 (ddt, 1H, J=15.0, 8.1, 2.5 Hz), 2.59 (ddt, 1H, J=15.0, 8.1, 2.5 Hz). MS (EI) m/z=174 ([M]+, 100%). HRMS (EI) Calcd. for C11H10O2: 174.0681. Found: 174.0677.

후처리

  1. customNitrogen was bubbled into the solution for 15 min
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated to a brown oil

출처 및 근거

ORD 기록
ord-102420b016204a699014c908bf046c20
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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