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

HRID 418952Notes

Reaction equation

HRID 418952 reaction equation
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]

Participants

4

Reactant 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, compound

Product 1

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

Procedure

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).

Workup

  1. concentrationconcentrate
  2. customreaction under vacuum and flash chromatograph

Sources & evidence

ORD record
ord-aca86e55c0e2414c9b5f8465dc0d507e
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

Loading…