All Notebooks | Help | Support | About
13th December 2016 @ 03:08

Outcome

The product was successfully synthesised and taken directly to the next step.

Rationale

Repeat attempt with ethyl ester starting material.

Procedure

AEW 321-1 (506 mg, 1.33 mmol, 1 equiv.) was dissolved in anhydrous THF (6 mL) and cooled to 0 oC. LiAlH4 (1 M in THF, 1.33 mL, 1.33 mmol, 0.64 equiv.) was added dropwise and the reaction mixture stirred for 10 min at 0 oC, then at rt overnight.

The reaction was cooled to rt, then in an ice bath. LAH was quenched with ethyl acetate dropwise, then a saturated solution of Rochelle's slat was added. The mixture was stirred at 0 oC, then at rt for 1.5 h.

The organic layer was separated and the aqueous layer extracted with ethyl acetate (2 x). The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product as a yellow oil (406 mg, 97%).

 

Strings

O=C(OCC)C(N(C)C)C1=CC(F)=C(F)C=C1

to

OCC(N(C)C)C1=CC(F)=C(F)C=C1

InChI=1S/C12H15F2NO2/c1-4-17-12(16)11(15(2)3)8-5-6-9(13)10(14)7-8/h5-7,11H,4H2,1-3H3

to

InChI=1S/C10H13F2NO/c1-13(2)10(6-14)7-3-4-8(11)9(12)5-7/h3-5,10,14H,6H2,1-2H3

Attached Files
AEW 322-1.rxn
AEW 322-1.png
AEW 322-1.cdxml