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Sodium Hydroxide → HCID 10330609, 화합물

HRID 2235836
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HRID 2235836 반응식
C([O:3][C:4](=[O:17])[CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+]>CCO.O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[CH:6]([CH2:5][C:4]([OH:17])=[O:3])[CH2:7][CH2:8]2
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 10263432Ethyl 2-(5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate

생성물 1

HCID 10330609HCID 10330609, 화합물수율 83.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of the crude ester (416 g, 1.77 mol) prepared in Example 2 in EtOH (1 L), was added a solution of NaOH (142 g, 3.54 mol) in water (1.5 L). The reaction mixture was heated to reflux, during which time the color changed to dark red, and the reaction became homogeneous. After 1 h, the reaction was cooled to rt, and the EtOH was removed under reduced pressure. The remaining basic aqueous layer was washed with Et2O (3×500 mL), then acidified with HCl (conc. aqueous solution) to pH˜4 at which point an oily residue formed. The mixture was then extracted with Et2O (4×500 mL), the combined extracts washed with water (2×300 mL) and brine, and then dried over Na2SO4. Filtration and evaporation of the solvents under reduced pressure gave the title compound (305 g, 83%) as a yellow solid after drying for 12 h under vacuum. 1H NMR (CDCl3) δ 7.34 (d, 1H), 6.71 (s, 1H), 6.65 (dd, 1H), 3.71 (s, 3H), 3.47 (m, 1H), 2.80 (m, 3H), 2.35 (m, 2H), 1.71 (m, 1H). MS (CI) m/z 207 [M+H]+.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux, during which time the color
  3. customthe EtOH was removed under reduced pressure
  4. washThe remaining basic aqueous layer was washed with Et2O (3×500 mL)
  5. customformed
  6. extractionThe mixture was then extracted with Et2O (4×500 mL)
  7. washthe combined extracts washed with water (2×300 mL) and brine
  8. dry with materialdried over Na2SO4
  9. filtrationFiltration and evaporation of the solvents under reduced pressure

출처 및 근거

ORD 기록
ord-e20e93be414842d9b7a3491598a0bb97
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714004B2

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