Open KlementineJBS opened 2 months ago
TLC at 9.30am indicated formation of product but SM not yet consumed. Heated to 40 C from then.
TLC at 3 pm was cleaner/less streaking but still showed plenty of SM. added another 115 mg of DCAD.
No clear sign of product (1101) but product generally doesn't ionise as well as other things.
No obvious sign of SM (686.68) or singly-alkylated product (893.92) either - only triphenylphosphine oxide adducts as usual.
KBS51-2 RM.d.zip KBS51-2 RM.pdf
Obvious signs of desired product (peak at 4.77) but appears to be some of the singly-alkylated product as well - this seems to produce a shoulder to the 4.77 peak. No SM is evident via NMR.
Heated to 65 C from 11 am after TLC indicated SM was still present (despite LRMS and NMR suggesting otherwise).
Link to HIRAC and master page #174.
HIRAC KBS48 Mitsunobu reaction on linear amines.docx
Reaction scheme
Outcome