Iodoethane → HCID 67264596、化合物

反応式

[C:1]([O:5][C:6]([C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][O:14][C:15](=[O:17])[NH:16][C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:27][CH3:28]>CN(C=O)C.O>[C:1]([O:5][C:6]([C:8]1[CH:19]=[CH:18][C:11]2[CH2:12][CH2:13][O:14][C:15](=[O:17])[N:16]([CH2:27][CH3:28])[C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

実験手順

A mixture of 6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocycloheptene-3-carboxylic acid tert-butyl ester (1.1 g, 4.18 mmol), potassium carbonate (2.5 g, 18.1 mmol, 4.3 eq.) and iodoethane (1.67 mL, 20.87 mmol, 5 eq.) was stirred in DMF (20 mL) for 16 hours at 60° C. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried (sodium sulfate) and concentrated. Silica gel chromatography (0→20% ethyl acetate in hexanes) provided 5-ethyl-6-oxo-5,6,8,9-tetrahydro-7-oxa-5-aza-benzocycloheptene-3-carboxylic acid tert-butyl ester as pale solid in quantitative yield: 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.80 (dd, 1H), 7.28 (d, 1H), 4.48 (t, 2H), 3.91 (q, 2H), 3.00 (t, 2H), 1.59 (s, 9H), 1.23 (t, 3H).