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Sodium Hydroxide → HCID 86678080, 화합물

HRID 2369763
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HRID 2369763 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1([CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[C:23]2[CH:22]=[C:21]([C:24]#[C:25]C(C)(O)C)[CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][C:14]([C:30]#[C:31]C(C)(O)C)=[CH:15][CH:16]=2.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(O)C>[C:30]([C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[C:23](=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=3)[C:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[C:12]=2[CH:13]=1)#[CH:31]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67248833HCID 67248833, 화합물

생성물 1

HCID 86678080HCID 86678080, 화합물수율 58.2%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3776Isopropanol용매

실험 절차

To a solution of 4,4′-[9,9-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene-2,7-diyl]bis(2-methyl-3-butyn-2-ol) (0.363 g, 0.58 mmol) in 9 mL of toluene and 2 mL of i-PrOH, was added solid NaOH (0.15 g, 3.75 mmol). The mixture was heated under reflux for 1.5 h. After cooling, NaOH was filtered off and the solvents were evaporated and the residue was purified by column chromatography on silica gel (CH2Cl2/AcOEt 60:40) to yield 0.171 g (58%) of 2,7-diethynyl-9,9-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene, mp 68° C.; 1H NMR (CDCl3) δ 2.37 (t, 4H, J=7.8 Hz), 2.74 (t, 4H, J=7.2 Hz), 3.17 (s, 2H), 3.20 (m, 4H), 3.35 (s, 6H), 3.39 (m, 4H), 3.54-3.47 (m, 8H), 7.50 (dd, 2H, J=7.8 Hz, J=1.3 Hz), 7.55 (d, 2H, J=1.3 Hz). 7.63 (d, 2H, J=7.8 Hz); 13C NMR (CDCl3) δ 39.5, 51.3, 59.1, 65.9, 66.8, 70.0, 70.4, 71.8, 77.9, 84.1, 120.1, 121.2, 127.0, 131.7, 140.2, 149.3. Anal. Calcd for C31H38O6 (506.63): C, 73.49; H, 7.56. Found: C, 73.59; H, 7.64.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 h
  3. temperatureAfter cooling
  4. filtrationNaOH was filtered off
  5. customthe solvents were evaporated
  6. customthe residue was purified by column chromatography on silica gel (CH2Cl2/AcOEt 60:40)

출처 및 근거

ORD 기록
ord-3975aac985144bf5acb15e4947bfc054
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08709747B2

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