Lithium hydroxide, monohydrate → {3-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetic acid

HRID 422867노트

반응식

HRID 422867 반응식
[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=1)[O:26][CH2:27][C:28]([O:30]CC)=[O:29].O.[OH-].[Li+]>O1CCCC1.O>[O:1]=[C:2]1[C:10]2([CH2:14][O:13][C:12]3[CH:15]=[C:16]4[C:20](=[CH:21][C:11]2=3)[CH2:19][CH2:18][O:17]4)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:22][C:23]1[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=1)[O:26][CH2:27][C:28]([OH:30])=[O:29]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 45280396ethyl {3-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetate

생성물 1

HCID 45280397{3-[(2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)methyl]phenoxy}acetic acid수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of ethyl {3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetate (0.46 g, 0.98 mmol) in a mixture of tetrahydrofuran (30 mL) and water (15 mL) was added lithium hydroxide monohydrate (0.32 g, 2.3 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 16 h. The mixture was concentrated in vacuo to a small volume, diluted with water (15 mL), washed with diethyl ether (60 mL), and acidified with 37% hydrochloric acid to pH 1. A white precipitate was formed. The mixture was extracted with ethyl acetate (3×60 mL). The combined organic solution was washed with water (30 mL), brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford {3-[(2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)methyl]phenoxy}acetic acid (0.41 g, 95%): mp 95-96° C.; 1H NMR (300 MHz, CDCl3) 7.33-7.14 (m, 3H), 7.07-6.97 (m, 2H), 6.92 (br s, 1H), 6.88-6.77 (m, 2H), 6.48 (s, 1H), 6.42 (s, 1H), 5.08-4.95 (m, 2H), 4.88-4.79 (m, 1H), 4.74-4.67 (m, 1H), 4.63 (s, 2H), 4.57-4.48 (m, 2H), 3.09-2.89 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.2, 172.6, 161.8, 161.3, 157.9, 141.9, 137.6, 132.6, 130.1, 128.8, 123.9, 123.6, 120.9, 120.0, 118.9, 113.9, 113.7, 113.7, 109.3, 93.2, 80.5, 72.4, 64.7, 57.8, 44.0, 29.0; MS (ES+) m/z 444.0 (M+1).

후처리

  1. concentrationThe mixture was concentrated in vacuo to a small volume
  2. additiondiluted with water (15 mL)
  3. washwashed with diethyl ether (60 mL)
  4. customA white precipitate was formed
  5. extractionThe mixture was extracted with ethyl acetate (3×60 mL)
  6. washThe combined organic solution was washed with water (30 mL), brine (50 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bc67b00ad7314423a1e0fd416f129826
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101647B2

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