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Hydrochloric Acid → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid

HRID 418949
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HRID 418949 반응식
C[O:2][C:3]([CH:5]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([O:27][CH3:28])[CH:10]=2)=[O:4].CO.[OH-].[Li+].Cl>O1CCCC1>[CH3:28][O:27][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]([C:3]([OH:4])=[O:2])[CH:18]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH:17]1[CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 666520266-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

생성물 1

HCID 666519726-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-9-carboxylic acid수율 97.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (1.03 g, 2.71 mmol), Methanol (20.0 mL), tetrahydrofuran (2 mL), and lithium hydroxide aqueous (5 mL), stir at reflux. After 18 hours, add 5N HCl until reaction is acidic, then extract with ethyl acetate and wash with brine. Dry the organic phase with anhydrous sodium sulfate then concentrate to yield the titled compound (0.97 g, 97%) as a white solid. TLC Rf=0.41 in 3% methanol in DCM. 1H NMR (DMSO): 12.30 (s, 1H), 7.25 (m, 3H), 6.92 (m, 3H), 6.82 (dd, 1H, J=8.6, 2.4 Hz), 4.18 (d, 1H, J=12.3 Hz), 3.76 (m, 6H), 3.42 (dd, 1H, J=12.6, 2.4 Hz), 3.27 (s, 1H), 2.50 (m, 1H), 1.89 (m, 1H), 1.59 (m, 2H), 1.40 (m, 1H), 1.23 (m, 1H), 0.99 (m, 3H); MS m/z 322 (M−44, decarbonylation).

후처리

  1. temperatureat reflux
  2. customuntil reaction
  3. extractionextract with ethyl acetate
  4. washwash with brine
  5. dry with materialDry the organic phase with anhydrous sodium sulfate
  6. concentrationthen concentrate

출처 및 근거

ORD 기록
ord-1655596638bc44f989958bf0deab888d
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08093302B2

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