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

HRID 1965794ノート

反応式

HRID 1965794 の反応式
C([O:8][C:9]1[CH:36]=[CH:35][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3([CH2:26][O:25][C:24]4[CH:27]=[C:28]5[C:32](=[CH:33][C:23]3=4)[CH2:31][CH2:30][O:29]5)[C:15]2=[O:34])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3([CH2:26][O:25][C:24]4[CH:27]=[C:28]5[C:32](=[CH:33][C:23]3=4)[CH2:31][CH2:30][O:29]5)[C:15]2=[O:34])=[CH:35][CH:36]=1

参加物

5

反応物 1

HCID 593523251'-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one

生成物 1

HCID 593524451'-(4-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-2'(1'H)-one収率 94.6%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1′-[4-(benzyloxy)benzyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1H)-one (2.4 g, 5.1 mmol) and palladium on carbon (10% w/w, 0.49 g) in anhydrous methanol (10 mL) and ethyl acetate (50 mL) was hydrogenated at ambient temperature under a balloon pressure for 16 h. The mixture was filtered through a pad of diatomaceous earth The pad was washed with ethyl acetate (50 mL) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography and eluted with a 25% to 50% gradient of ethyl acetate in hexanes to afford 1′-(4-hydroxybenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one (1.86 g, 94%) as a colorless solid: mp 226-227° C.; 1H NMR (300 MHz, CDCl3) δ 7.25-7.13 (m, 4H), 7.06-6.99 (m, 1H), 6.87-6.82 (m, 1H), 6.78-6.72 (m, 2H), 6.44-6.41 (m, 2H), 5.27 (s, 1H), 4.88 (ABq, J=69.0, 15.3 Hz, 2H), 4.84 (ABq, J=82.9, 9.0 Hz, 2H), 4.55-4.46 (m, 2H), 2.96-2.86 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.2, 161.8, 161.3, 155.5, 142.1, 132.8, 128.8, 128.7, 127.5, 123.9, 123.5, 120.0, 119.9, 118.8, 115.8, 109.4, 93.3, 80.5, 72.4, 70.0, 57.8, 43.7, 28.9; MS (ES+) m/z 385.9 (M+1).

後処理

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth The pad
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluted with a 25% to 50% gradient of ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-937ca213010d4e0f8fda938a448f42bc
出典データセット
uspto-grants-2013_04
特許番号
US08415370B2

反応ノート

読み込み中…