Heptadecylamine → HCID 67247093, 화합물

HRID 2410244노트

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HRID 2410244 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 67247093HCID 67247093, 화합물수율 813.6%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

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온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8823fb03b7be4ed092c73f430ecb546c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816035B2

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