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Submitted by Althea Tsang and Matthew H. Todd, School of Chemistry, University of Sydney, NSW 2006, Australia. Checked by Victor Sun, Lakshmi Raj Baratha, Soo-Jean Park, same address.
TLC (hexane:ethyl acetate, 5:1) after 3.5 hours indicated only product and baseline spots. TLC after 23 h indicated slight appearance of second spot at Rf = 0.38.
1H NMR (CDCl3): Î´ 1.49 (9H, s, H9), 2.83 (2H, dd,J5.8, 5.8, H4), 3.64 (2H, dd,J5.8, 5.8, H3), 4.57 (2H, s, H1), 7.05 “ 7.35 (4H, m). IR (CHCl3) Î½max/cm-11682, 1419, 1173. m/z (ESI) 132.1 (100%).
Reference: Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalyzed lithiation, E. Alonso, D. J. Ramon and M. Yus,Tetrahedron1997,53, 14355-14368.
1) Original procedure used 1 N HCl wash as well as sat. NaHCO3 wash. No column chromatography.
2) Dilute NaHCO3 wash used in above procedure, working equally well.
3) Column in 1:1 hexane:ethyl acetate works equally well.