Heptadecylamine → HCID 67247093、化合物

HRID 2410244ノート

反応式

HRID 2410244 の反応式
Br[C:2]1(Br)[CH:6]=[CH:5][S:4][CH:3]1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C(O[Na])(C)(C)C.C1C=CC(P([C:32]2[C:41]([C:42]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=C[CH:49]=[C:48]4[C:43]=3[CH:44]=[CH:45][CH:46]=[CH:47]4)=C3[C:35]([CH:36]=[CH:37][CH:38]=[CH:39]3)=[CH:34][CH:33]=2)C2C=CC=CC=2)=CC=1.C(CCCCCCCCC[NH2:82])CCCCCCC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:32]([CH:41]([N:82]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:3]2[S:4][CH:5]=[CH:6][C:2]1=2)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

参加物

8

反応物 4

HCID 15791HeptadecylamineHCID 634876Binap, (A+-)-HCID 67246593HCID 67246593、化合物HCID 178418730sodium 2-methylpropan-2-olate

生成物 1

HCID 67247093HCID 67247093、化合物収率 813.6%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a solution of 3,3-dibromo-2,2′-bithiophene (4.92 g, 15.3 mmol), t-BuONa (3.54 g, 36.8 mmol), Pd2 dba3 (0.35 g, 0.382 mmol) and BINAP (0.95 g, 1.53 mmol) in toluene (38 mL) under an argon atmosphere was added 9-octylnonylamine (4 g, 15.7 mmol). The reaction mixture was subsequently stirred at 110° C. over a period of 7 hours. The reaction mixture was allowed to cool to room temperature followed by the addition of water. The organic layer was removed and the remaining aqueous phase extracted several times with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. Purification by column chromatography using hexanes as the eluant afforded the title compound as a light green solid (5.2 g, 81% yield): mp: 60° C.; GC-Ms: 417.5; 1H NMR (400 MHz, CDCl3, ppm) δ: 7.11(d, 2H), 7.02-7.01(d, 2H), 4.23-4.19(m, 1H), 2.08(m, 2H), 1.85-1.80(m, 2H), 1.22-1.07(m, 24 H), 0.86-0.82(t, 6 H); 13C NMR (100 MHz, CDCl3, ppm) δ: 144.2, 122, 4, 114.9, 59.9, 35.4, 31.9, 29.4, 29.3, 26.7, 22.8, 14.2.

後処理

  1. temperatureto cool to room temperature
  2. customThe organic layer was removed
  3. extractionthe remaining aqueous phase extracted several times with diethyl ether
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography

出典と根拠

ORDレコード
ord-8823fb03b7be4ed092c73f430ecb546c
出典データセット
uspto-grants-2014_08
特許番号
US08816035B2

反応ノート

読み込み中…