Dicyclohexylcarbodiimide → HCID 86754820, compound

Participants

Reaction Steps

--The hydroxy ester 60 (410 mg, 1.25 mol), 4-tetradecyloxybenzoic acid (417 mg, 1.25 mmol), DCC (257 mg, 1.25 mmol) and dimethylaminopyridine (cat.) in dry dichloromethane (15 ml) were stirred for 48 h at room temperature. Flash silica was added and the solvent was removed in vacuo and the residue was purified by flash chromatography (10% ethyl acetate-light petroleum) to give the ester 61 (230 mg, 28%) (from EtOH/MeOH), transitions/° C. I TGB(fog) TGB(C or A) SC 88 SCferri1 81.4 SCferri2SCanti 69 K (m.p. 85.4° C.); [α]D19 +20.2° (c 1.9 in CHCl3); νmax /cm-1 (KBr) 2880, 1705 (CO), 1690 (CO), 1610, 1460, 1290, 1240, 1195, 1110 and 830; δ 0.88 (6H, m), 1.20-1.60 (33H, m), 1.60-1.90 (4H, m), 4.05 (2H, t, J 6, OCH2), 5.22 (1H, sext, J 6, OCHMe), 6.98 (2H, J 8, 3'- and 5'-H), 7.37 (2H, d, J 8, ArH), 8.16 (2H, d, J 8, ArH), 8.60(2H, d, J8, 2'- and 6'-H) and 9.31 (2H,s,); m/z 642 (M+ -2), 419,317,265 and 121.

Provenance & Evidence