Convenient preparation of aryl ether derivatives using a sequence of functionalized polymers

Tetrahedron Letters

Volumn 44, Issue 26, 2003, Pages 4873-4876

  Lizarzaburu, Mike E ^a   Shuttleworth, Stephen J ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BASE; ETHER DERIVATIVE; POLYMER; REAGENT; SCAVENGER; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

LETHRINIDAE;

EID: 0037565118     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01117-1     Document Type: Article

References (19)

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8. Lizarzaburu M.E., Shuttleworth S.J. Tetrahedron Lett. 43:2002;2157.
9. Commercially-available from Sigma-Aldrich Inc., catalogue #36,645-5.
10. For examples of halogenation mediated by supported triphenylphosphine, see: (a) Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721; (b) Dabbagh, A.-H.; Mallakpour, S. E.; Faghihi, K. Ir. Polym. J. 1998, 7, 149.
11. For examples of halogenation mediated by supported triphenylphosphine, see: (a) Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshdel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721; (b) Dabbagh, A.-H.; Mallakpour, S. E.; Faghihi, K. Ir. Polym. J. 1998, 7, 149.
12. Commercially-available from Polymer Laboratories Ltd., catalogue #3414-1679.
13. Commercially-available from Polymer Laboratories Ltd., catalogue # 3404-4679.
14. Percentage conversion to the desired products was determined by HPLC at 220 nm and 254 nm using an Agilent 1100 LC/MSD VL ESI system.
15. Typical protocol involved treating a methanolic solution of the substrate with wet palladium on carbon (Aldrich catalogue # 33,010-8, 3 weight equivalents) with 5% formic acid over a 12 h period. Following removal of the inorganic residue by filtration, the product was isolated following evaporation of the filtrate under reduced pressure.
16. Commercially-available from Polymer Laboratories Ltd., catalogue # 3413-4679.
17. Commercially available from Novabiochem Inc.; catalogue # 01-64-0177.
18. Commercially available from Novabiochem Inc.; catalogue # 01-64-0317.
19. 5S requires 365.10.