Sodium hydride → 6-bromo-2,2-di(but-3-en-1-yl)-2,3-dihydro-1H-inden-1-one

HRID 1503444ノート

反応式

HRID 1503444 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:15][CH2:16][CH:17]=[CH2:18]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH2:4][CH2:3][CH:2]=[CH2:10])([CH2:15][CH2:16][CH:17]=[CH2:18])[C:8]2=[O:11])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1397781-Indanone, 6-bromo-HCID 5432164-Iodobut-1-ene

生成物 1

HCID 581972806-bromo-2,2-di(but-3-en-1-yl)-2,3-dihydro-1H-inden-1-one収率 32.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 6-bromo-1-indanone (0.5330 g, 2.52 mmol) in dry THF (10 mL) was added NaH (0.3380 g, 60% in a mineral oil, 8.45 mmol) at 0° C. under nitrogen. After being stirred for 10 min, 4-iodobut-1-ene (1.3450 g, 7.39 mmol) was added and then the mixture was stirred at ambient temperature for 20 h. The reaction mixture was cooled to 0° C., quenched with 1 N HCl, extracted with ethyl acetate, and dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.1304 g of 6-bromo-2,2-di(but-3-en-1-yl)-2,3-dihydro-1H-inden-1-one. LC-MS tR=2.33 min in 3 min chromatography, m/z 319, 321 (MH1); 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.67 (d, J=8 Hz, 1H), 7.33 (d, J=8 Hz, 1H), 5.76-5.66 (m, 2H), 4.94-4.87 (m, 4H), 2.98 (s, 2H), 1.98-1.63 (m, 8H); 13C NMR (100 MHz, CDCl3) δ 209.23, 151.43, 138.85, 137.85, 137.54, 127.94, 126.75, 121.55, 114.81, 52.87, 37.28, 36.58, 28.54.

後処理

  1. stirringthe mixture was stirred at ambient temperature for 20 h
  2. customquenched with 1 N HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customAfter the solvents were evaporated
  6. customthe residue was purified by chromatography on silica gel
  7. washeluted with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-2f02be58d27841c98bffc2dfb3bcab86
出典データセット
uspto-grants-2015_12
特許番号
US09212153B2

反応ノート

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