2'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid → Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate

HRID 1662416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662416
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](O)=[O:15])=[CH:10][C:9]=1[C:17]([O:19][CH3:20])=[O:18]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1

Komponenten

3

Edukt 1

HCID 577067632'-Fluoro-2-((methyloxy)carbonyl)-1,1'-biphenyl-4-carboxylic acid

Produkt 1

HCID 57705859Methyl 2'-fluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylateAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a stirred solution of 66.32B (0.90 g, 3 mmol) in THF (33 mL) at 0° C. was added borane-THF complex (7 mL, 7 mmol, 1.0M). The reaction was allowed to warm to 23° C. and stirred for 7 hours. The reaction mixture was then concentrated in vacuo. The reaction was diluted with 1N HCl and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 66.32C as a colorless solid (0.850 g, 100% yield).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionThe reaction was diluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationfiltering
  6. customthe organic solvent was removed under reduced pressure
  7. customthe product was then purified on silica gel (0-40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4ff16315cd374508bee4474bfb6c5402
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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