(6-Bromo-1,3-dioxaindan-5-yl)methanol → 3-hydroxy-3-[6-(hydroxymethyl)-1,3-benzodioxol-5-yl]-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 545746ノート

反応式

HRID 545746 の反応式
Br[C:2]1[C:3]([CH2:11][OH:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[Li]CCCC.[CH2:18]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[C:24]1=[O:33])[CH2:19][CH2:20][CH2:21][CH3:22]>C1COCC1>[OH:32][C:25]1([C:2]2[C:3]([CH2:11][OH:12])=[CH:4][C:5]3[O:9][CH2:8][O:7][C:6]=3[CH:10]=2)[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:24]1=[O:33]

参加物

5

反応物 3

HCID 225817(6-Bromo-1,3-dioxaindan-5-yl)methanolHCID 15810921-Pentyl-1H-indole-2,3-dioneHCID 178418339Butyllithium

生成物 1

HCID 120044023-hydroxy-3-[6-(hydroxymethyl)-1,3-benzodioxol-5-yl]-1-pentyl-1,3-dihydro-2H-indol-2-one収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-75 °C

実験手順

To a solution of (6-bromo-1,3-benzodioxol-5-yl)methanol (Mann, J., et al, J. Chem. Soc. Perkin Trans. 1 (1984):2081-8) (1.27 g, 5.50 mmol) in THF (45.0 mL) was added n-BuLi (5.00 mL, 2.0 M, 10.0 mmol) dropwise at −75° C. The reaction mixture was stirred at −75° C. for 45 min followed by the addition of a solution of 1-pentyl-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in THF (20.0 mL) at −75° C. The resulting mixture was stirred at ambient temperature for 12 hrs and quenched with ammonium chloride solution (5.00 mL). More ethyl acetate and water were added and separated. The organic layer was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with 50% EtOAc:Hexanes to yield the title compound (0.29 g, 25%) as a solid: 1H NMR (300 MHz, CDCl3) δ 7.38-7.24 (m, 2H), 7.11 (t, 1H), 6.91 (d, 1H), 6.81 (s, 1H), 6.43 (s, 1H), 5.90-5.87 (m, 2H), 4.77 (dd, 2H), 3.75-3.56 (m, 2H), 1.75-1.58 (m, 2H), 1.26-1.35 (m, 2H), 0.89-0.83 (m, 3H); 13C NMR (75 MHz, CDCl3) δ 177.8, 147.4, 147.2, 142.8, 133.5, 132.2, 131.1, 130.1, 125.3, 123.8, 111.4, 109.2, 108.1, 101.5, 79.5, 64.7, 40.4, 29.0, 26.8, 22.3, 13.9; MS (ES+) m/z 352.1 (M−17).

後処理

  1. stirringThe resulting mixture was stirred at ambient temperature for 12 hrs
  2. customquenched with ammonium chloride solution (5.00 mL)
  3. additionMore ethyl acetate and water were added
  4. customseparated
  5. concentrationThe organic layer was concentrated in vacuo to dryness
  6. washeluting with 50% EtOAc

出典と根拠

ORDレコード
ord-2cff584ffa2b4bc193660a268ea7d910
出典データセット
uspto-grants-2011_05
特許番号
US07935721B2

反応ノート

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