Water → 1'-[3-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

HRID 422848

反応式

HRID 422848 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]3=[CH:14][C:15]4[CH2:19][CH2:18][O:17][C:16]=4[CH:20]=[C:12]3[O:11][CH2:10]2)[C:2]1=[O:21].[H-].[Na+].[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]Br)[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([O:31][C:32]1[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=1)[CH2:38][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:10][O:11][C:12]3[CH:20]=[C:16]4[C:15](=[CH:14][C:13]2=3)[CH2:19][CH2:18][O:17]4)[C:2]1=[O:21])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15020473-Benzyloxybenzyl bromideHCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one

生成物 1

HCID 593524861'-[3-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one収率 82%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3′-indolin]-2′-one (1.0 g, 3.6 mmol) in dry N,N-dimethylformamide (18 mL) was added sodium hydride (60% in mineral oil, 0.17 g, 4.3 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 1 h, cooled in an ice/water bath, and 1-(benzyloxy)-3-(bromomethyl)benzene (1.4 g, 5.0 mmol) in dry N,N-dimethylformamide (2 mL) was added dropwise. The mixture was stirred at ambient temperature for 16 h. Water (200 mL) and ethyl acetate (200 mL) were added to the mixture. The organic solution was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic solution was washed with brine (150 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (hexanes/ethyl acetate 3:1) to afford 1′-[3-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (1.4 g, 82%) as a colorless solid: mp 66-68° C.; 1H NMR (300 MHz, CDCl3) δ 7.43-7.14 (m, 8H), 7.06-6.99 (m, 1H), 6.97-6.87 (m, 3H), 6.81-6.75 (m, 1H), 6.48 (s, 1H), 6.43 (s, 1H), 5.10-5.00 (m, 3H), 4.85-4.75 (m, 1H), 4.84 (ABq, 2H), 4.56-4.47 (m, 2H), 2.98-2.88 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 177.9, 161.8, 161.3, 159.2, 142.1, 137.4, 136.6, 132.7, 129.9, 128.7, 128.6, 128.0, 127.5, 123.8, 123.4, 120.2, 119.9 (2C), 118.8, 114.0, 113.9, 109.3, 93.2, 80.5, 72.3, 70.0, 57.7, 44.0, 29.0; MS (ES+) m/z 476.1 (M+1).

後処理

  1. temperaturecooled in an ice/water bath
  2. stirringThe mixture was stirred at ambient temperature for 16 h
  3. customThe organic solution was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic solution was washed with brine (150 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (hexanes/ethyl acetate 3:1)

出典と根拠

ORDレコード
ord-29cd61e58b0e4458a71758128f23805b
出典データセット
uspto-grants-2012_01
特許番号
US08101647B2

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