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30th April 2012 @ 01:33
START: 30/04/12
FINISH:

Scheme%20KAB21-9.png

Hazard and Risk Assessment
As for KAB25-2 here:
Hazard and Risk Assessment KAB25-2


Previous Experiments
Yb(OTf)3 catalysed PS to give 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB25-1)
Lewis acid-catalyst screen for the PS reaction to give KAB21 and KAB24
Yb(OTf)3 catalysed PS to give 6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline (KAB25-3)
Synthesis of N-benzylidene-N-phenethylamine (KAB18-2)

Following Experiments

Chemical Information
N-[2-(3,4-Dimethoxyphenyl)ethyl]-1-phenylmethanimine (KAB19-2) SMILES: O(c1ccc(cc1OC)CC/N=C/c2ccccc2)C, InChI: InChI=1S/C17H19NO2/c1-19-16-9-8-14(12-17(16)20-2)10-11-18-13-15-6-4-3-5-7-15/h3-9,12-13H,10-11H2,1-2H3/b18-13+, InChIKey: HEYKSOUNCDDROU-QGOAFFKASA-N

Procedure
(All glassware was ovendried prior to use.)
30/04/12. KAB19-2 (52 mg, 193 mmol, 1 equiv.) was dissolved in dry toluene (1.2 mL) before the addition of well dried 3Å powdered MS. Yb(OTf)3 (25 mg, 0.040 mmol, 0.2 equiv) was added under an atmosphere of nitrogen before the reaction mixture was reflux heated, under nitrogen, to 110 °C from 14:50.

Monitoring the Reaction Progress by TLC
All TLCs were eluted with 15%, MeOH/DCM, v/v and stained with ninhydrin.
TLC of reaction mixture (1 h)
TLC of reaction mixture (18 h)


Summary and Conclusion


References
[1] K. Manabe, D. Nobutou, S. Kobayashi, Bioorg. Med. Chem. 2005, 13, 5154-5158.
[2] M. J. V. Eynden, K. Kunchithapatham, J. P. Stambuli, Journal of Organic Chemistry 2010, 75, 8542-8549.


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NOTES 30/04/12
- Reaction mixture went yellower after addition of Yb.
- Yellow faded after 15 min
Flask = 47.1232
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Linked Posts
Attached Files
Scheme KAB21-9
TLC of reaction mixture (1 h)
TLC of reaction mixture (18 h)