Benzyl Bromide → 7-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

HRID 1359015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359015
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 140682207-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7-Benzyloxy-3,4-dihydro-1(2H)naphthalenone was prepared by treating 7-hydroxy-1-tetralone (5.91 g, 36.4 mmol) and caesium carbonate (13 g, 40.0 mmol) in dry DMF (100 ml) and under N2 with benzylbromide (6.22 g, 4.33 ml, 36.4 mmol). The reaction was stirred for 3 h and the mixture then filtered and the filtrate concentrated in vacuo. The oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml), the organic layer separated, dried (MgSO4) and concentrated in vacuo. Trituration of the resultant solid with diethylether-hexane (1:1, 200 ml) gave the desired compound as a white solid (6.57 g) m.p. 86-87°0. MS (EI, 60V) 252 (M+, 100%).

Aufarbeitung

  1. filtrationthe mixture then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe oily residue was partitioned between ethyl acetate (200 ml) and brine (200 ml)
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-785644a7b80648f2a9b91f396aa336d1
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599908B1

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