Ethyl chloroformate → Ethyl 1,4-dimethoxy-3-methyl-2-naphthoate

HRID 15718

Reaktionsgleichung

Reaktionsgleichung von HRID 15718
C([Li])CCC.Br[C:7]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[O:20][CH3:21].Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1>[CH3:19][O:18][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:20][CH3:21])=[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16]=1[CH3:17]

Komponenten

5

Edukt 3

HCID 10928Ethyl chloroformateHCID 2922402-Bromo-1,4-dimethoxy-3-methylnaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 11369352Ethyl 1,4-dimethoxy-3-methyl-2-naphthoateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

n-Butyl lithium (1.6M in hexanes, 4.1 ml, 6.56 mmol) was added dropwise to 2-bromo-1,4-dimethoxy-3-methylnaphthalene (1.537 g, 5.47 mmol) in tetrahydrofuran (30 ml) at −50° C. The reaction was stirred for 30 min at −50° C. before dropwise addition of ethyl chloroformate (1 ml, 10.46 mmol). The reaction was allowed to warm to 0° C. over 18 h quenched by addition of hydrochloric acid (2N) and extracted with ethyl acetate. The extract was dried (Na2SO4) and the solvent evaporated under vacuum. The residue was purified by SPE (silica, 10 g) eluting with 10% ethyl acetate in cyclohexane to give ethyl 1,4-dimethoxy-2-methylnaphthalene-3-carboxylate (1.33 g, 89%).

Aufarbeitung

  1. customquenched by addition of hydrochloric acid (2N)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (Na2SO4)
  4. customthe solvent evaporated under vacuum
  5. customThe residue was purified by SPE (silica, 10 g)
  6. washeluting with 10% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-68ac42a1003a457896b8b3eb493ce566
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732622B2

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