Dimethylformamide → 6-Hydroxy-2-naphthaldehyde

HRID 374868

Reaktionsgleichung

Reaktionsgleichung von HRID 374868
[Li+].CCC[CH2-].Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([OH:17])[CH:11]=[CH:10]2.C([Li])(C)(C)C.CN(C)P(N(C)C)(N(C)C)=O.CN(C)[CH:36]=[O:37]>C1COCC1>[OH:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:36]=[O:37])[CH:16]=[CH:15]2

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 12679HexamethylphosphoramideHCID 271446-Bromo-2-naphthalenolHCID 61028n-Butyl lithiumHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 27641106-Hydroxy-2-naphthaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step a) N-Butyllithium (35.9 mL, 89.7 mmol) was added dropwise to a cold (-78° C.) solution of 6-bromo-2-naphthol (20.0 g, 89.7 mmol) in THF (200 mL). After stirring for 10 minutes, tertbutyllithium (52.76 mL, 89.7 mmol) was added dropwise. The mixture was stirred for 30 min at -78° C, and two hours at -20° C. Then, hexamethylphosphoramide (15.6 mL, 89.7 mmol) was added to the reaction mixture. After stirring for 20 minutes. N,N-dimethylformamide (6.94 mL, 89.7 mmol) was added dropwise. The mixture was allowed to come to room temperature, stirred for 1 hour, and quenched with aqueous ammonium chloride. The mixture was poured into water, acidified with 2N HCL and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexane/EtOAc 3/1 ), gave a yellow solid (12.5 g, 81% yield, m.p. 173°-174 ° C.).

Aufarbeitung

  1. stirringThe mixture was stirred for 30 min at -78° C
  2. customtwo hours
  3. customat -20° C
  4. stirringAfter stirring for 20 minutes
  5. customto come to room temperature
  6. stirringstirred for 1 hour
  7. customquenched with aqueous ammonium chloride
  8. additionThe mixture was poured into water
  9. extractionextracted with EtOAc
  10. dry with materialThe organic extracts were dried over MgSO4
  11. customEvaporation and purification by flash chromatography (hexane/EtOAc 3/1 )

Quellen und Nachweise

ORD-Eintrag
ord-45a5ead73b5d4e6f824c9900e697d11b
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05482968

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