Phenethylthiophenol → HCID 178420258, 화합물

HRID 1895566노트

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HRID 1895566 반응식
O[C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13](O)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2.[CH2:25]([C:33]1C=CC=C[C:34]=1[SH:39])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[I-].[Zn+2].[I-].C(Cl)Cl>[CH2:25]([CH2:33][CH2:34][S:39][C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13]([S:39][CH2:34][CH2:33][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2)[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

5

반응물 2

HCID 67226359PhenethylthiophenolHCID 178521537HCID 178521537, 화합물

생성물 1

HCID 178420258HCID 178420258, 화합물수율 71%

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of trans-6,13-dihydroxy-6,13-dihydropentacene (1.0 g, 3.20 mmol) and zinc iodide (1.02 g, 3.20 mmol) were added successively dry CH2Cl2 (100 mL) and phenethylthiophenol (0.77 g, 7.03 mmol) at RT under an argon atmosphere. The resulting mixture was stirred at RT for 2 h, and then quenched with H2O. The mixture was extracted with CH2Cl2, and the organic layer was washed with brine and dried over anhyd. Na2SO4. After evaporation of solvents, the residue was purified by column chromatography on silica gel eluted with n-hexanes-CH2Cl2 (2:1) to give product as white solids in 71% yield (1.13 g). 1H NMR (500 MHz, CDCl3): δ 7.80 (m, 4H), 7.70 (s, 4H), 7.46 (m, 4H), 7.29 (t, 4H, J=7.56 Hz), 7.20 (m, 6H), 5.24 (s, 2H), 2.90 (s, 8H). LDI-MS m/z: 552 [M+], 416 [M+-SCH2CH2C6H5], 280 [M+-2(SCH2CH2C6H5)].

후처리

  1. customquenched with H2O
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. customdried over anhyd
  5. customAfter evaporation of solvents
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluted with n-hexanes-CH2Cl2 (2:1)
  8. customto give product as white solids in 71% yield (1.13 g)

출처 및 근거

ORD 기록
ord-75465c89ac2d436ea923bb5810711ca3
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513466B2

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