Potassium Fluoride → 4-Phenyl-6-[(z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

HRID 218256Notes

Reaction equation

HRID 218256 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11](/[CH:13]=[CH:14]\[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[C:10]([O:27][Si](C(C)(C)C)(C)C)=[C:9]([O:35][Si](C(C)(C)C)(C)C)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+]>CO.CN(C)C=O.C(O)(=O)C.C(OC)(C)(C)C>[C:1]1([C:7]2[CH:12]=[C:11](/[CH:13]=[CH:14]\[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[C:10]([OH:27])=[C:9]([OH:35])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 522689Potassium FluorideHCID 601306744-Phenyl-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy)benzene

Product 1

HCID 99997064-Phenyl-6-[(z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 15413tert-Butyl methyl etherSolventHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

To a solution of 24 (0.05 g, 0.082 mmol) in methanol:dimethylformamide 1:1 (2 mL), acetic acid was added (0.025 mL, 0.41 mmol) followed by potassium fluoride (0.024 mg, 0.41 mmol). The mixture was stirred for 6 hours then diluted with tertbutylmethyl ether (50 mL) and washed with water (10 mL) then brine (50 mL), then dried over sodium sulphate. The solvent was removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 6:4+1% AcOH) to give 0.097 g of ZSB-80:

Workup

  1. washwashed with water (10 mL)
  2. dry with materialbrine (50 mL), then dried over sodium sulphate
  3. customThe solvent was removed under reduced pressure
  4. customto give a crude which
  5. customwas purified by column (cyclohexane:AcOEt 6:4+1% AcOH)
  6. customto give 0.097 g of ZSB-80

Sources & evidence

ORD record
ord-6784459a6cf742198cf58dd9d711a4f5
Source dataset
uspto-grants-2012_06
Patent number
US08198302B2

Reaction notes

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