Dimethylformamide → [6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-acetonitrile

HRID 418950Notes

Reaction equation

HRID 418950 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17]OS(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.[C-:37]#[N:38].[K+].CN(C=O)C.C(OCC)(=O)C>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][C:37]#[N:38])[CH:12]([C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 72309434Toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester

Product 1

HCID 66652095[6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-acetonitrileYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 (0.224 g, 0.44 mmol), KCN (0.172 g, 2.65 mmol), and DMF (4 mL), and stir under nitrogen atmosphere at 100° C. After 2 hours, add ethyl acetate and water. Separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.139 g, 87%) as a white foam. TLC Rf=0.46 in 4:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.31 (m, 1H), 7.24 (d, 2H, J=8.8 Hz), 6.96 (m, 3H), 6.84 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.59 (m, 1H), 3.34 (s, 1H), 3.18 (dd, 1H, J=12.3, 3.1 Hz), 2.90 (dd, 1H, J=17.2, 4.4 Hz), 2.51 (m, 2H), 1.98 (m, 1H), 1.66 (m, 2H), 1.48 (m, 2H), 1.14 (m, 3H).

Workup

  1. customSeparate the organic phase
  2. washwash with brine
  3. dry with materialDry the organic phase with anhydrous sodium sulfate and flash chromatograph

Sources & evidence

ORD record
ord-9b6f0b7fe4ac46a08d4c8d1d83b8082b
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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