Hexanal → 6-(hexyl{4-[(4-propylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 551959노트

반응식

HRID 551959 반응식
[CH3:1][C:2]1([CH3:32])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH3:30])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:11][C:5]=2[C:4](=[O:31])[O:3]1.[CH:33](=O)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>>[CH2:33]([N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH3:30])=[CH:26][CH:27]=2)=[CH:16][CH:15]=1)[C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([CH3:1])([CH3:32])[O:3][C:4](=[O:31])[C:5]=2[CH:11]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

참가 물질

3

반응물 2

HCID 6184HexanalHCID 575545222,2-dimethyl-6-({4-[(4-propylphenyl)ethynyl]benzyl}amino)-4H-1,3-benzodioxin-4-one

생성물 1

HCID 575545016-(hexyl{4-[(4-propylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one수율 75%

실험 절차

The title compound was prepared following procedure described in Example 23, step b) from 2,2-dimethyl-6-({4-[(4-propylphenyl)ethynyl]benzyl}amino)-4H-1,3-benzodioxin-4-one (660 mg; 1.55 mmol) and hexanal (Aldrich, 279.41 μl, 2.33 mmol). Purification of the crude (880 mg) by flash chromatography using silica gel (EtOAc/c-Hex, 5:95 then 10:90) gave 590 mg (75%) of the title compound as a beige powder. HPLC, Rt.: 6.37 min (purity: 61.9%), 1H NMR (CDCl3) δ: 7.42 (m, 4H), 7.12-7.19 (m, 5H), 6.78 (m, 2H), 4.48 (s, 2H), 3.34 (t, J=7.6 Hz, 2H), 2.57 (t, J=7.8 Hz, 2H), 1.68 (s, 6H), 1.61 (m, 4H), 1.24 (m, 6H), (0.91 (t, J=7.3 Hz, 3H), 0.86 (t, J=6.7 Hz, 3H).

후처리

  1. customThe title compound was prepared following procedure
  2. customPurification of the crude (880 mg) by flash chromatography

출처 및 근거

ORD 기록
ord-93f74db81f0b45d4bd55eda725844ea5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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