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15th January 2015 @ 03:25

GitHub Issue #276 and #275 previously (#235 and #236)

See related attempts: Synthesis of methyl 2-(3,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetate (AEW 109-1) and Synthesis of methyl 2-(3,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)acetate (AEW 109-2)

Procedure:

AEW 173-1 (2 g, 12.0 mmol, 1 equiv.) and DHP (1.86 mL, 1.72 g, 20.4 mmol, 1.7 equiv.) were dissolved in anhydrous CH2Cl2 (8.5 mL) under Argon (NB exotherm so placed quickly in ice bath, in future cool before addition of DHP) and cooled to 0 ˚C. PPTS (74 mg, 0.30 mmol, 0.03 eq.) was added and the reaction mixture was stirred at 0 ˚C for 3 h (black solution) and then at rt for 20 h. 

CH2Cl2 (80 mL) was added and the resulting solution was shaken with portions of ice-cold water (3 x 10 mL) and once with saturated NaHCO(10 mL). The organic phase was dried (MgSO4) and filtered, and the solvent was removed under reduced pressure.

 

Hazard and Risk Assessment:

Reference:

New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-,Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands
Peter Huszthy, Masatoshi Oue, Jerald S. Bradshaw, Cheng Y. Zhu, Ting

J. Org. Chem., Vol. 57, No. 20, 1992 5383-5394

http://pubs.acs.org/doi/pdf/10.1021/jo00046a020?source=chemport

Attached Files
AEW 219-1.cdx
AEW 219-1.png