Boron tribromide → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketone

HRID 1883265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883265
C[O:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([C:17](=[O:19])[CH3:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 30179161-(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethyl-2-naphthyl)ethan-1-one2×

Produkt 1

HCID 2266995,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl methyl ketoneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Intermediate 3, 10.7 g, 41.2 mmol) in CH2Cl2 (500 mL) at 0° C. was added BBr3 (49.5 mL, 1.0 M in CH2Cl2) via syringe pump over 10 min. The mixture was stirred at 0° C. for 2 h and was quenched with ice-H2O and extracted with Et2O (×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (CH2Cl2) to give the title compound as a brown solid (7.6 g, 75%).

Aufarbeitung

  1. customwas quenched with ice-H2O
  2. extractionextracted with Et2O (×3)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-c26792f6ec9b4a26b3c5a26a47170c37
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759547B1

Notizen zur Reaktion

Wird geladen…