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

반응식

HRID 422848 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-29cd61e58b0e4458a71758128f23805b
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101647B2

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