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Pentachlorophenol → pentachlorophenyl (2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoate

HRID 77347
Notes
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Reaction equation

HRID 77347 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 53248608(2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoic acid

Product 1

HCID 53248609pentachlorophenyl (2E)-3-[4-[(diethoxyphosphinyl)oxy]phenyl]-but-2-enoateYield 72.2%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-45336e3cdda04410bbba6192b600804b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841257B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes