Tetrahydrofuran → 9-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418952노트

반응식

HRID 418952 반응식
COC1[CH:4]=[C:5]2[C:14](=[CH:15]C=1)[CH:13](COS(C1C=CC(C)=CC=1)(=O)=O)[CH:12]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[CH3:37][Mg]Br.[O:40]1[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH2:14]([CH:13]1[CH:12]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[CH:11]2[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)[C:5]2[C:41]1=[CH:42][CH:43]=[C:44]([O:40][CH3:37])[CH:4]=2)[CH3:15]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl esterHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 666519649-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene수율 81%

실험 절차

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.151 g, 0.30 mmol), methyl magnesium bromide (0.46 mL, 1.40 mmol), Li2CuCl4 (150 uL), and tetrahydrofuran (3 mL), and stir under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum and flash chromatograph using 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.085 g, 81%) as a white foam. TLC Rf=0.60 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.32 (s, 1H), 7.24 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.42 (m, 1H), 3.23 (s, 1H), 3.08 (dd, 1H, J=12.1, 3.3 Hz), 2.49 (d, 1H, J=13.7 Hz), 1.93 (m, 2H), 1.67 (m, 1H), 1.57 (m, 2H), 1.44 (d, 2H, J=8.8 Hz), 1.19 (m, 3H), 0.62 (t, 3H, J=7.3 Hz).

후처리

  1. concentrationconcentrate
  2. customreaction under vacuum and flash chromatograph

출처 및 근거

ORD 기록
ord-aca86e55c0e2414c9b5f8465dc0d507e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093302B2

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