Dimethylformamide → 3-Ethyl-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

HRID 218247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218247
[CH2:1]([C:3]1[C:4]([O:31][Si](C(C)(C)C)(C)C)=[C:5]([O:23][Si](C(C)(C)C)(C)C)[C:6](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[CH:7][CH:8]=1)[CH3:2].[F-].[K+].CN(C)C=O>CO.C(O)(=O)C.C(OC)(C)(C)C>[CH2:1]([C:3]1[C:4]([OH:31])=[C:5]([OH:23])[C:6](/[CH:9]=[CH:10]\[C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)=[CH:7][CH:8]=1)[CH3:2]

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 522689Potassium Fluoride2×HCID 601306903-Ethyl-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-di(tert-butyldimethylsilyloxy)benzene

Produkt 1

HCID 102460563-Ethyl-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-dihydroxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel3×HCID 887MethanolLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To a solution of 13 (0.15 g, 0.268 mmol) in methanol (2 mL), acetic acid was added acetic acid (0.032 mL, 0.563 mmol) followed by potassium fluoride (0.033 mg, 0.563 mmol). Dimethylformamide was then added (0.5 mL) and the mixture was stirred for 16 hours then more acetic acid (0.04 mL) and KF (0.033 mg) were added and the mixture stirred for 48 hours. The mixture was then diluted with tertbutylmethyl ether (50 mL) and washed with water (10 mL). The aqueous layer was re-extracted, the combined organic layers were washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to give a crude which was purified by column (cyclohexane:AcOEt 8:2+1% AcOH) to give 0.05 g of ZSB-76:

Aufarbeitung

  1. stirringthe mixture stirred for 48 hours
  2. washwashed with water (10 mL)
  3. extractionThe aqueous layer was re-extracted
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. customthe solvent removed under reduced pressure
  7. customto give a crude which
  8. customwas purified by column (cyclohexane:AcOEt 8:2+1% AcOH)
  9. customto give 0.05 g of ZSB-76

Quellen und Nachweise

ORD-Eintrag
ord-448263d52c2b4732a8990edcfc19fc3c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198302B2

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