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Allyl bromide → 1,2,3,4Tetrahydro-8-methoxy-2-oxo-3-(2-propenyl)-1-naphthalene-carboxylic Acid Methyl Ester

HRID 2270503
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2270503
[CH3:1][O:2][C:3]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[CH2:8][CH2:7][C:6]1=[O:17])=[O:4].[Li+].[CH3:19][CH:20]([N-]C(C)C)[CH3:21].C(Br)C=C>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH3:16])[CH2:8][CH:7]([CH2:21][CH:20]=[CH2:19])[C:6]1=[O:17])=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 99916161,2,3,4-Tetrahydro-8-methoxy-2-oxo-1-naphthalene carboxylic acid methyl ester

Produkt 1

HCID 100847181,2,3,4Tetrahydro-8-methoxy-2-oxo-3-(2-propenyl)-1-naphthalene-carboxylic Acid Methyl EsterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 10.2 g (43.5 mmol) 1,2,3,4-tetrahydro-8-methoxy-2-oxo-1-naphthalene carboxylic acid methyl ester in 108 mL of THF in a three-neck, round-bottomed flask, equipped with a dropping funnel, was added dropwise 63.8 mL (95.7 mmol) of LDA (1.5 M in cyclohexane) at −30° C. to −40° C. under a nitrogen atmosphere. The solution was allowed to warm to 0° C. and 6.0 mL (69.6 mmol) of allylbromide was added. After stirring the mixture for one hour at room temperature, TLC analysis showed no starting material remaining. The reaction was quenched with 3N hydrochloric acid to pH 2-3 and extracted with ethyl acetate (2×1 L). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was purified by liquid chromatography on 800 g silica gel 60 (230-400 m), eluting with hexane-acetone (3:1), and collecting 40 mL fractions. Fractions 36-63 gave 10.3 g (87%) of pure title compound as a yellow oil.

Aufarbeitung

  1. customThe reaction was quenched with 3N hydrochloric acid to pH 2-3
  2. extractionextracted with ethyl acetate (2×1 L)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by liquid chromatography on 800 g silica gel 60 (230-400 m)
  8. washeluting with hexane-acetone (3:1)
  9. customcollecting 40 mL fractions

Quellen und Nachweise

ORD-Eintrag
ord-55b90f5518b64d8582a71cc0a2b16ca9
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06331636B1

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