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

HRID 10747

反応式

HRID 10747 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 219810903-(Dihydro-2-furanyl)benzaldehyde収率 40%

試薬・触媒・溶媒 3

HCID 178418851HCID 178418851、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-102420b016204a699014c908bf046c20
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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