Tetrahydrofuran → Methyl 2-fluoro-4-[(E)-2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate

HRID 1836867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836867
O1CCCC1.[CH:6]([C:8]1[C:17]([CH3:18])=[CH:16][C:15]2[C:14]([CH3:20])([CH3:19])[CH2:13][CH2:12][C:11]([CH3:22])([CH3:21])[C:10]=2[CH:9]=1)=O.[F:23][C:24]1[CH:38]=[C:37]([C:39](OC)=O)[CH:36]=[CH:35]C=1CP(=O)(OCC)OCC.[H-].[Na+].[C:45]([O:48][CH2:49]C)(=[O:47])[CH3:46]>>[F:23][C:24]1[CH:38]=[C:37](/[CH:39]=[CH:6]/[C:8]2[C:17]([CH3:18])=[CH:16][C:15]3[C:14]([CH3:20])([CH3:19])[CH2:13][CH2:12][C:11]([CH3:22])([CH3:21])[C:10]=3[CH:9]=2)[CH:36]=[CH:35][C:46]=1[C:45]([O:48][CH3:49])=[O:47]

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2266983,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxaldehydeHCID 23498922Methyl 4-[(diethoxyphosphoryl)methyl]-3-fluorobenzoate

Produkt 1

HCID 23498968Methyl 2-fluoro-4-[(E)-2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoateAusbeute 54 %

Versuchsvorschrift

A 0° C., 3M tetrahydrofuran solution of 350 mg (1.62 mmol) of 2-formyl-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalene and 541 mg (1.78 mmol) of diethyl 2-fluoro-4-carbomethoxybenzylphosphonate was treated with 84 mg (2.10 mmol, 60% wt. in mineral oil) NaH in 10 mg portions over 10 minutes. The reaction mixture was stirred at room temperature for 2 hours before diluting with ethyl acetate and washing with brine. The organic extracts were dried over magnesium sulfate, concentrated in vacuo and triturated with methanol to provide 330 mg (54%) Methyl 2-fluoro-4-[(E)-2-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate.

Aufarbeitung

  1. washwashing with brine
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customtriturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-363a86138e7a41cfba90b8ebe4c9f360
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777418B2

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