Water → HCID 22565244、化合物

HRID 25847

反応式

HRID 25847 の反応式
B(Br)(Br)Br.[CH2:5]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]#[N:24])=[CH:17][C:16]=2[CH2:25][CH:26]([CH3:28])[CH3:27])[CH:12]=[CH:11][C:10]=1[C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[C:31]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)[CH:30]=1)[CH:6]([CH3:8])[CH3:7].O>C(Cl)Cl>[OH:35][C:32]1[CH:33]=[CH:34][C:29]([C:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]#[N:24])=[CH:17][C:16]=3[CH2:25][CH:26]([CH3:27])[CH3:28])=[CH:14][C:9]=2[CH2:5][CH:6]([CH3:8])[CH3:7])=[CH:30][C:31]=1[CH2:37][C:38]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 225652543-(2',2''-Diisobutyl-4-methoxy-3-naphthalen-1-ylmethyl-[1,1':4', 1'']-terphenyl-4''-yl)propionitrile

生成物 1

HCID 22565244HCID 22565244、化合物収率 62.85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

1.02 ml (1.02 mmol, 3.00 eq.) of a 1 M solution of BBr3 in CH2Cl2 was added to a solution of 192.9 mg (0.34 mmol) 3-(2′,2″-Diisobutyl-4-methoxy-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]-terphenyl-4″-yl)propionitrile (76) in 20 ml dry CH2Cl2 at 0° C. via syringe. After that the solution was stirred for 3 h at 0° C. and then for 12 h at r.t. The reaction mixture was then added to water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (hexanes/EtOAc (2+1)) yielded 117.9 mg (0.21 mmol, 62.85%) 3-(4-Hydroxy-2′,2″-diisobutyl-3-naphthalen-1-ylmethyl-[1,1′:4′,1″]terphenyl-4″-yl)propionitrile (32) as a colorless oil. Rf (hexanes/EtOAc (2+1))=0.37. 1H-NMR (500 MHz, CDCl3): δ=0.59 (d, 6H, J=6.62 Hz, 2*CH3), 0.70 (d, 6H, J=6.78 Hz, 2*CH3), 1.50 (m, 1H, CH), 1.65 (m, 1H, CH), 2.32 (d, 2H, J=7.25 Hz, CH2), 2.47 (d, 2H, J=7.25 Hz, CH2), 2.62 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.94 (t, 2H, J=7.41 Hz, CH2CH2CN), 4.47 (s, 2H, CH2Naphthyl), 480 (s, 1H, OH), 6.86 (d, 1H, J=8.36 Hz), 6.98-7.16 (m, 9H), 7.38 (m, 1H), 7.43-7.48 (m, 2H), 7.73 (dm, 1H, J=8.73 Hz), 7.83 (m, 1H), 8.06 (m, 1H). MS (EI): m/z=552 (30), 551 (65), 446 (21), 419 (21), 178 (19), 155 (15), 149 (24), 142 (18), 141 (100), 128 (28), 97 (23), 85 (26), 83 (25), 71 (39), 69 (30), 57 (74), 55 (35). HR-MS (EI): Calcd. for C40H41NO: 551.318814. Found: 551.318768.

後処理

  1. waitfor 12 h at r.t
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

出典と根拠

ORDレコード
ord-19b39617ccb74e98a116d56ba23727a3
出典データセット
uspto-grants-2005_02
特許番号
US06858600B2

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