Sodium Hydroxide → t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

HRID 1378840

Reaktionsgleichung

Reaktionsgleichung von HRID 1378840
[Si:1]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH:18]=[CH2:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B.C1C[O:27]CC1.[O-][O-].[Na+].[Na+].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][C:9]1[C:10]([CH2:20][CH2:21][CH3:22])=[CH:11][C:12]([CH2:18][CH2:19][OH:27])=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 14803Sodium peroxideHCID 2723981Borane;tetrahydrofuranHCID 19080390t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzene

Produkt 1

HCID 19080442t-Butyldimethylsilyloxy-2,6-dipropyl-4-(2-hydroxyethyl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 475 mg (1.48 mmol) of the product of Step B in 3 mL of THF at 0 ° C. was added 1.6 mL (1.62 mmol) of a 1N borane/THF solution. After 1 hour TLC indicated that the starting material had been consumed. The reaction mixture was quenched with 3 drops of methanol and then 0.70 mL (6.22 mmol) of 30% sodium peroxide and 6.2 mL (6.2 mmol) of 1N sodium hydroxide were added. After two hours the reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was then dried over sodium sulfate, filtered and concentrated. Hash chromatography (silica gel, hexane/ethyl acetate 4:1) gave 265 mg of the title compound as a clear oil.

Aufarbeitung

  1. customhad been consumed
  2. customThe reaction mixture was quenched with 3 drops of methanol
  3. washwashed with water and brine
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be54b93fb24b49eda2c4342074f1c3ce
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668176

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