Reaktion #566782

Reaktionsgleichung

Water

Propiolactone

65c

2-(2-Ethyl-7-hydroxy-3-(o-phenylbenzyl)indolizin-1-yl)glyoxylylamide

potassium t-butoxide

→

70b

2-(7-(2-Carboethoxyethyloxy)-2-ethyl-3-(o-phenylbenzyl)indolizin-1-yl)glyoxylamide

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe mixture was washed with ethyl acetate
2. 2
   FiltrationThe precipitate was collected with filtration

Vorschrift

Propiolactone (25 mg, 0.336 m mol) was added dropwise to a solution of 65c (133.7 mg, 0.336 m mol) and potassium t-butoxide (37.6 mg, 0.336 m mol) in tetrahydrofuran (4 ml) under nitrogen. The mixture was stirred for 21 hr. Water was added. The mixture was washed with ethyl acetate. The aqueous phase was acidified with hydrochloric acid. The precipitate was collected with filtration to give 70b, 96.2 mg (60.9%). Mp, 99-108° C. (dec.). IR nmax (KBr) 3700-2400, 3182, 2968, 2931, 1719, 1677, 1644 cm−1. 1H NMR (CDCl3) δ 1.19 (3H, t, J=7.5 Hz), 2.80 (2H, t, J=6.3 Hz), 2.92 (2H, q, J=7.5 Hz), 4.08 (2H, s), 4.30 (2H, t, J=6.3 Hz), 6.35 (1H, dd, J=2.7, 7.8 Hz), 6.84 (1H, d, J=7.8 Hz), 7.12-7.53 (9H, m), 7.72 (1H, d, J=2.7 Hz). Analyses: Calc'd for C28H26N2O5.1.2H2O: C, 68.34; H, 5.82; N, 5.69. Found: C, 68.40; H, 5.76; N, 5.43.

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