Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → 4-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcohol

HRID 37233

Reaktionsgleichung

Reaktionsgleichung von HRID 37233
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[CH2:19])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][C:7]1[CH:16]=[CH:15][C:10]([CH2:11][OH:12])=[CH:9][C:8]=1[CH2:17][CH:18]=[CH2:19])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 544131774-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcoholAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a magnetically stirred solution of 8.523 g (28.0 mmol) of the product from Step C in 35 mL of anhydrous THF was added 15.0 mL of a 1.0M solution of lithium aluminum hydride in THF, and the reaction mixture was stirred under a nitrogen atmosphere for 2 hours. At this point, the reaction was quenched by cautious addition of 10 mL water, the resulting precipitate was dissolved by addition of 1.0N is hydrochloric acid and the product was extracted into ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo to afford 7.258 g (93%) of the title compound.

Aufarbeitung

  1. customAt this point, the reaction was quenched by cautious addition of 10 mL water
  2. dissolutionthe resulting precipitate was dissolved by addition of 1.0N
  3. extractionthe product was extracted into ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e4a9f528123b42bc910262d591370551
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420133

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