2-Methyl-2-butene → 4,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid

HRID 367301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 367301
[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH:15]=[O:16])([CH3:14])[O:13][C:9]=2[CH:8]=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]=1[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])([CH3:4])([CH3:3])[CH3:2].P([O-])(O)(O)=[O:27].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:1]([C:5]1[C:10]2[CH2:11][C:12]([CH3:14])([C:15]([OH:27])=[O:16])[O:13][C:9]=2[CH:8]=[C:7]([C:17]([CH3:18])([CH3:20])[CH3:19])[C:6]=1[O:21][Si:22]([CH3:25])([CH3:24])[CH3:23])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 105532-Methyl-2-buteneHCID 232880364,6-Di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuranHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Produkt 1

HCID 232880354,6-Di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a solution of 0.5 g of 4,6-di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran in 5 ml of t-butyl alcohol were added 5 ml of a saturated aqueous sodium dihydrogenphosphate solution and 0.73 ml of 2-methyl-2-butene, and the mixture was cooled to -5° C. To this solution was added dropwise a solution of 0.14 g of sodium chlorite in 5 ml of distilled water, and the mixture was stirred for 20 minutes, then further stirred at room temperature for 15 minutes. The reaction solution was extracted with diethyl ether, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was recrystallized from hexane to give 0.38 g of 4,6-di-t-butyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran-2-carboxylic acid as a colorless powder (yield 73%).

Aufarbeitung

  1. stirringfurther stirred at room temperature for 15 minutes
  2. extractionThe reaction solution was extracted with diethyl ether
  3. washthe combined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-823cd5f5eaa84674b78a37455a2d85c4
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133279

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