4-Methylmorpholine → (4-(Pyridin-4-yl)phenyl)methanol

HRID 395704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 395704
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([O-])=[O:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Na+].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 23673507Sodium 4-(pyridin-4-yl)benzoate

Produkt 1

HCID 2795556(4-(Pyridin-4-yl)phenyl)methanolAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of sodium 4-(4-pyridyl)benzoate (500 mg, 2.26 mmol), and N-methylmorpholine (0.250 mL, 2.26 mmol) in tetrahydrofuran (12 mL) was treated with ethyl chloroformate (0.216 mL, 2.26 mmol). After 0.25 h, the mixture was treated with sodium borohydride (256 mg, 6.79 mmol) followed by methanol (24 mL) dropwise. After 0.5 h, the mixture was treated with 10% aqueous acetic acid and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide. The aqueous layer was extracted twice with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo to yield 140 mg of the title compound which was used without further purification.

Aufarbeitung

  1. waitAfter 0.5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialthe combined extracts were dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60694848b49f48048039bf82c36c71d1
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

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