Pentachlorophenol → HCID 53248609, 화합물

HRID 77347

반응식

HRID 77347 반응식
[CH2:1]([O:3][P:4]([O:19][CH2:20][CH3:21])([O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[CH3:18])=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Cl:22][C:23]1[C:28](O)=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([O:3][P:4]([O:19][CH2:20][CH3:21])([O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[CH3:18])=[CH:14]/[C:15]([O:17][C:28]2[C:27]([Cl:30])=[C:26]([Cl:31])[C:25]([Cl:32])=[C:24]([Cl:33])[C:23]=2[Cl:22])=[O:16])=[CH:11][CH:12]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 53248608HCID 53248608, 화합물

생성물 1

HCID 53248609HCID 53248609, 화합물수율 72.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 10b (2.0 g, 6.4 mmol), pentachlorophenol (1.9 g, 7.0 mmol), DCC (1.6 g, 7.7 mmol) and DMAP (0.08 g, 0.64 mmol) in 100 mL of EtOAc was stirred at room temperature for 24 h. The mixture was filtered through celite and the solvent removed in vacuo. The crude product was purified by silica gel chromatography eluting with 25% EtOac-hexanes to give 2.6 g (72%) of 11b1 as white solid. 1H NMR (CDCl3, 300 MHz) δ 1.26-1.32 (m, 6H), 2.54 (d, J=1.2 Hz, 3H), 4.12-4.21 (m, 4H), 6.34 (d, J=1.2 Hz, 1H), 7.2 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H). 11C NMR (CDCl3, 75.0 MHz) δ 16.0, 16.1, 18.4, 64.8, 64.8, 68.9, 113.4, 120.2, 120.3, 128.0, 128.1, 131.2, 131.9, 137.8, 141.9, 144.3, 152.1, 160.6, 161.9. HRMS (M+H) calc, 560.9362; found, 560.9197.

후처리

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent removed in vacuo
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with 25% EtOac-hexanes

출처 및 근거

ORD 기록
ord-45336e3cdda04410bbba6192b600804b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841257B2

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