반응 #56646

반응 방정식

1-(2-trimethylsilanyloxyethoxy)cyclobutanecarbonitrile

hydroxylamine

diethyl acetylenedicarboxylate

→

2-{[1-(2-hydroxyethoxy)cyclobutanecarboximidoyl]-aminooxy}but-2-enedioic acid diethyl ester

용매

EtOH

반응 조건

후처리

1. 1
   온도cooled to room temperature
2. 2
   농축This mixture was concentrated in vacuo
3. 3
   기타to obtain 6.16 g of a crude brownish oil

실험 절차

A solution of 1-(2-trimethylsilanyloxyethoxy)cyclobutanecarbonitrile (3.5 g, 16.4 mmol) and 50% aqueous hydroxylamine (1.08 g, 16.4 mmol) in EtOH (16 mL) was stirred in an oil bath heated at 80° C. for 2.5 hrs and then cooled to room temperature. To a solution was added drop-wise diethyl acetylenedicarboxylate (2.93 g, 17.2 mmol) in an ice-bath and the mixture stirred at room temperature for 5 hrs. This mixture was concentrated in vacuo to obtain 6.16 g of a crude brownish oil containing intermediate 25: 1H NMR (500 MHz, CDCl3) δ: 1.19-1.38 (6 H, m) 1.72-1.86 (2 H, m) 2.06-2.24 (2 H, m) 2.29-2.49 (2 H, m) 3.26-3.38 (2 H, m) 3.65-3.76 (2H, m) 4.11-4.19(2 H, m) 4.24-4.38(2 H, m) 5.67(0.25 H, s) 5.85 (0.5 H, s). HRMS (M+H) calcd for C15H25N2O7 345.1662, found 345.1648.

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