Methanol → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

HRID 418945Notes

Reaction equation

HRID 418945 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:18]([C:19]2[CH:24]=[CH:23][C:22](OC)=[CH:21][CH:20]=2)C2C(CCCC2OC)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:4].[CH3:29][O-:30].[Na+].CO.O1[CH2:38][CH2:37][CH2:36][CH2:35]1.[C:39]([O:42][CH2:43][CH3:44])(=O)C>>[CH3:1][O:2][C:3]([CH:5]1[CH:18]([C:36]2[CH:35]=[CH:44][C:43]([O:42][CH3:39])=[CH:38][CH:37]=2)[CH:19]2[CH:24]([CH2:23][CH2:22][CH2:21][CH2:20]2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([O:30][CH3:29])[CH:10]=2)=[O:4]

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 66651957Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

Product 1

HCID 666520266-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl esterYield 99%

Procedure

Combine methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (9.95 g, 26.15 mmol), NaOMe (0.283 g, 5.23 mmol), methanol (32 mL), and tetrahydrofuran (125 mL), and stir under nitrogen atmosphere at 40° C. After 3 hours, concentrate reaction to dryness and add ethyl acetate. Wash with water and then brine, dry the organic phase with anhydrous sodium sulfate and concentrate to yield the titled compound (10.03 g, 99%) as a yellow-white solid. TLC Rf=0.25 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.27 (d, 2H, J=8.8 Hz), 7.20 (d, 1H, J=8.4 Hz), 6.99 (m, 1H), 6.90 (d, 2H, J=8.4 Hz), 6.77 (dd, 1H, J=8.4, 2.6 Hz), 4.36 (d, 1H, J=12.3 Hz), 3.84 (m, 6H), 3.60 (s, 3H), 3.54 (dd, 1H, J=12.6, 2.9 Hz), 3.36 (s, 1H), 2.51 (d, 1H, J=14.1 Hz), 2.01 (m, 1H), 1.72 (m, 2H), 1.45 (m, 2H), 1.11 (m, 3H).

Workup

  1. concentrationconcentrate
  2. customreaction to dryness
  3. washWash with water
  4. dry with materialbrine, dry the organic phase with anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-d02de06e82aa43eb9c8e3a57d4cc1e74
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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