Acetylresorcinol → 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate

HRID 985494

Reaktionsgleichung

Reaktionsgleichung von HRID 985494
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([OH:18])[CH:16]=1)(=[O:13])[CH3:12].[CH:22]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C1COCC1>[C:11]([O:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:17]([O:18][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])[CH:16]=1)(=[O:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 5055AcetylresorcinolHCID 139400Triisopropylsilyl chlorideHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 114610083-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetateAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium bis(trimethylsilyl)amide (73 ml, 73 ml, 1M solution in THF) was added dropwise to a solution of resorcinol monoacetate (10 g, 65.7 mmol) in THF (100 ml) at 78° C. under argon. The solution was stirred for 10 minutes and then triisopropylsilyl chloride (15.5 ml, 73 mmol) was added via syringe. After stirring at room temperature overnight, the mixture was partitioned between water and ethyl acetate. The organic layer was dried, filtered and evaporated under vacuum to yield 13 g of crude 3-[1,1-bis(Methylethyl)-2-methyl-1-silapropoxy]phenyl acetate which was used in the next step without further purification. NMR 1H Cl3CD δ: 7.19 (t, 1H, J=8 Hz), 6.75 (m, 1H), 6.68 (m, 1H), 6.63 (t, 1H, J=4 Hz), 2.29 (s, 3H), 1.25 (m, 3H), 1.11 (d, 18H, J=7.0 Hz).

Aufarbeitung

  1. stirringAfter stirring at room temperature overnight
  2. customthe mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-05f88b98537b45a9a32b7f014cc764ab
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872730B2

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