Acetic Acid → 3-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

HRID 1675922노트

반응식

HRID 1675922 반응식
[OH-].[K+].[CH3:3][C@@:4]12[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]1[C@H:16]1[C@@H:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:22])=[CH:12][C:13]=3[CH2:14][CH2:15]1)[CH2:6][CH2:5]2.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH:28]=O.C(O)(=O)C>C(O)C>[OH:22][C:11]1[CH:10]=[CH:9][C:8]2[CH:7]3[CH:16]([CH2:15][CH2:14][C:13]=2[CH:12]=1)[CH:17]1[C:4]([CH3:3])([C:20](=[O:21])[C:19](=[CH:28][C:27]2[CH:30]=[C:31]([O:35][CH3:36])[C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=2)[CH2:18]1)[CH2:5][CH2:6]3

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5870EstroneHCID 68583,4,5-TrimethoxybenzaldehydeHCID 14797Potassium Hydroxide

생성물 1

HCID 50130353-Hydroxy-13-methyl-16-(3,4,5-trimethoxy-benzylidene)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Potassium hydroxide (1.0 g) was added to a solution of estrone (1.350 g, 2.0 mmol) and 3,4,5-trimethoxybenzaldehyde (1.00 g, 5.10 mmol) in ethanol (50 ml) at room temperature. The resulting dark brown solution was stirred at this temperature for 4 h, then glacial acetic acid (ca. 2.5 ml) was added with stirring. The colour changed to yellow and a white solid precipitated. The solid was filtered off and washed with water (50 ml), ethanol (20 ml), diethyl ether (50 ml) and hexane and recrystallised from ethanol. Yield: 2.063 g (92%) light yellow crystals. 1H-NMR (CDCl3, 400 MHz), δ: 1.00 (s, 3H), 1.40-1.78 (m, 5H), 2.00-2.11 (m, 2H), 2.26-2.34 (m, 1H), 2.38-2.56 (m, 2H), 2.84-3.04 (m, 3H), 3.90 (s, 3H), 3.91 (s, 6H), 4.93 (s, 1H, —OH), 6.60 (d, J=2.3 Hz, 1H), 6.66 (dd, J=8.2, 2.3 Hz, 1H), 6.80 (s, 2H), 7.17 (d, J=8.2 Hz, 1H), 7.40 (s, 1H). 13C-NMR (CDCl3, 100 MHz), δ: 15.0, 26.4, 27.2, 29.4, 32.1, 38.4, 44.4, 48.2, 49.0, 56.6, 61.3, 108.2, 113.2, 115.6, 126.6, 131.3, 131.9, 133.9, 135.2, 137.9, 139.7, 153.4, 154.0, 209.9. LRMS (FAB+): 449.3 (100, [M+H]+). LRMS (FAB−): 447.3 (100, [M−H]−). HRMS (FAB+): 448.223763.

후처리

  1. stirringwith stirring
  2. customprecipitated
  3. filtrationThe solid was filtered off
  4. washwashed with water (50 ml), ethanol (20 ml), diethyl ether (50 ml) and hexane
  5. customrecrystallised from ethanol

출처 및 근거

ORD 기록
ord-44e32c34f08e4d2a8284e59d14ca5d91
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003783B2

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