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

HRID 2427560노트

반응식

HRID 2427560 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  1. temperaturewas heated
  2. temperatureat reflux

출처 및 근거

ORD 기록
ord-4113793e606849b4af7ade7a1db477bc
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968570B2

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