Water → 4-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-one

HRID 346223

Reaktionsgleichung

Reaktionsgleichung von HRID 346223
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>ClCCl>[Si:19]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Produkt 1

HCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-hydroxy-1-indanone (594 mg) and triethylamine (0.7 ml) in dry dichloromethane (10 ml) was added tert-butyldimethylsilyl chloride (724 mg) in several portions at 0° C. The mixture was stirred overnight at ambient temperature and then poured into a mixture of water (30 ml) and dichloromethane (20 ml). The separated organic layer was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate solution, succeedingly. The solution was dried and evaporated in vacuo. The residue was purified by columnchromatography on silica gel eluted by dichloromethane to give 4-(tert-butyldimethylsilyl)oxy-1-indanone (1.002 g) as an oil.

Aufarbeitung

  1. washThe separated organic layer was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate solution
  2. customThe solution was dried
  3. customevaporated in vacuo
  4. customThe residue was purified by columnchromatography on silica gel
  5. washeluted by dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-68a272ff6fcc4efa8c9eb1d0f9c0475c
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061718

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