Aluminium lithium hydride → 2-(hydroxymethyl)-3,4-dihydronaphthalen-1(2H)-one

HRID 1296109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296109
C[O:2][C:3]([C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9](CC(C)(C)C)=[CH:10][CH:11]=2)[C:6]=1[OH:20])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:20]

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 577186237-(2,2-Dimethyl-propyl)-1-hydroxy-3,4-dihydro-naphthalene-2-carboxylic acid methyl ester

Produkt 1

HCID 214445072-(hydroxymethyl)-3,4-dihydronaphthalen-1(2H)-oneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of 7-(2,2-Dimethyl-propyl)-1-hydroxy-3,4-dihydro-naphthalene-2-carboxylic acid methyl ester (2.49 g, 9.07 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (1 M in tetrahydrofuran, 9 mL, 9 mmol). The reaction mixture was stirred at 0° C. for 2 h and then quenched with saturated ammonium chloride and ethyl acetate. The resulting emulsion was filtered through diatomaceous earth. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Flash column chromatography (silica gel, 10–20% ethyl acetate/hexanes) provided hydroxymethyl tetralone (1.55 g, 70%): 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=1.4 Hz, 1H), 7.27 (dd, J=7.8, 1.4 Hz, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.00–3.90 (m, 1H), 3.85–3.75 (m, 1H), 3.20–3.10 (m, 1H), 3.08–2.90 (m, 2H), 2.75–2.60 (m, 1H), 2.52 (s, 2H), 2.15–2.05 (m, 1H), 2.00–1.85 (m, 1H), 0.90 (s, 9H).

Aufarbeitung

  1. customquenched with saturated ammonium chloride and ethyl acetate
  2. filtrationThe resulting emulsion was filtered through diatomaceous earth
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined extracts were washed with saturated sodium chloride
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4e015a300004e03a22c980959f4407a
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244725B2

Notizen zur Reaktion

Wird geladen…