Citric Acid → (2',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol

HRID 416173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416173
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:5]([CH2:17][CH3:18])[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=1)[CH3:2].CO.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[CH2:17]([C:5]1[CH:6]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=1)[CH3:18]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 593425632',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde

Produkt 1

HCID 59342594(2',6'-Diethyl-4'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanolAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2′,6′-diethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-carbaldehyde (2.86 g, 7.64 mmol) in a mixed solvent of methanol (8 mL) and tetrahydrofuran (16 mL) was ice-cooled, sodium borohydride (90%, 0.161 g, 3.82 mmol) was added, and the mixture was stirred for 2 hr under nitrogen atmosphere. The reaction mixture was treated with 10% aqueous citric acid solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:80-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (2.41 g, yield 84%) as colorless crystals.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:80-80:20)
  7. customthe obtained crystals were recrystallized from heptane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8b33c1dba41248de96bcb8be413b48b6
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088821B2

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