Dimethylformamide → HCID 66652115, compound

HRID 418967Notes

Reaction equation

HRID 418967 reaction equation
Br[C:2]1[C:15]([OH:16])=[CH:14][C:13]2[CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)[CH:6]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:5][C:4]=2[CH:3]=1.C[O-].[Na+].CN([CH:30]=[O:31])C>C(OCC)(=O)C>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([CH:6]2[CH2:5][C:4]3[CH:13]=[C:14]([O:31][CH3:30])[C:15]([OH:16])=[CH:2][C:3]=3[CH:12]3[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]3)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 66652277HCID 66652277, compound

Product 1

HCID 66652115HCID 66652115, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 2-Bromo-9-(4-hydroxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol (chiral) (0.033 g, 0.09 mmol), CuCl2 (0.008 g, 0.06 mmol), 5 M NaOMe (in methanol, 1.5 ml), DMF (0.5 ml) and heat 15 hours at 110° C. Cool, add ethyl acetate and wash with 1N HCl, then water. Dry organic layer over anhydrous sodium sulfate and remove solvent in vacuo. Chromatograph over silica gel 2× first with 20% ethyl acetate/hexanes, then 5-20% ethyl acetate/hexanes to yield the titled compound (0.010 g, 100%). 1H NMR (CDCl3): 7.21 (d, J=8.4 Hz, 2H), 7.0 (s, 1H), 6.85 (d, J=8.8 Hz, 2H), 6.69 (s, 1H), 3.91 (s, 3H), 3.2 (m, 4H), 2.85 (dd, J=4 and 11 Hz, 1H), 2.45 (d, J=14.9 Hz, 1H), 2.1-0.8 (m, 7H). MS m/z 323(M−1).

Workup

  1. temperatureCool
  2. washwash with 1N HCl
  3. customDry organic layer over anhydrous sodium sulfate and remove solvent in vacuo

Sources & evidence

ORD record
ord-54b59fdd9ddd489f80acaf54a1fe96af
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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