Ethyl Acetate → 2-[1-(4-Phenoxyphenyl)-ethyl]-2,3-dihydroisoindol-1-one

HRID 2427560ノート

反応式

HRID 2427560 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH2:16])[CH3:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:18][C:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]Br.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH:14]([N:16]2[CH2:26][C:21]3[C:20](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:19]2=[O:18])[CH3:15])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 592071-(4-Phenoxyphenyl)ethan-1-amineHCID 2734813Methyl 2-(bromomethyl)benzoate

生成物 1

HCID 579494992-[1-(4-Phenoxyphenyl)-ethyl]-2,3-dihydroisoindol-1-one収率 44.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 1-(4-phenoxyphenyl)ethylamine (213 mg, 1 mmol), 2-bromomethyl-benzoic acid methyl ester (250 mg, 1.1 mmol), and K2CO3 (1 g, 7.2 mmol) in toluene (10 mL) was heated at reflux with stirring for 16 h. Workup and silica gel column chromatography using a gradient of hexanes to 30% ethyl acetate in hexanes afforded 2-[1-(4-phenoxyphenyl)-ethyl]-2,3-dihydroisoindol-1-one (146 mg, 44%). GC/MS gave: m/z (rel.int.) 329 (M+, 46), 314 (100), 196 (8) and 77 (8). 1H NMR (300 MHz, CDCl3): δ 1.68 (d, 3H), 4.03 (d, 1H), 4.34 (d, 1H), 5.80 (q, 1H), 6.98 (br t, 4H), 7.10 (t, 1H), 7.49 (dt, 2H), 7.33 (br m, 5H), 7.88 (dd, 1H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux

出典と根拠

ORDレコード
ord-4113793e606849b4af7ade7a1db477bc
出典データセット
uspto-grants-2011_06
特許番号
US07968570B2

反応ノート

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