Tetrahydrofuran → 4-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-ol

HRID 15629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15629
[OH:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=3)=[C:12]([CH3:25])[CH:11]=2)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.O1CCCC1.[BH4-].[Na+]>CO>[OH:24][CH2:23][C:19]1[CH:18]=[C:17]([C:13]2[C:12]([CH3:25])=[CH:11][C:10]([O:9][CH2:8][C:2]3([OH:1])[CH2:7][CH2:6][S:5][CH2:4][CH2:3]3)=[CH:15][C:14]=2[CH3:16])[CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 231574564'-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2',6'-dimethylbiphenyl-3-carbaldehyde

Produkt 1

HCID 231571864-({[3'-(hydroxymethyl)-2,6-dimethylbiphenyl-4-yl]oxy}methyl)tetrahydro-2H-thiopyran-4-olAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.12 g, 5.95 mmol) in a mixed solvent of tetrahydrofuran (8 mL) and methanol (4 mL) was added sodium borohydride (0.225 g, 5.95 mmol) under ice-cooling, and the mixture was stirred at the same temperature for 20 min. The reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (1.87 g, yield 88%) as colorless crystals.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure, aqueous ammonium chloride solution
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1ce25ae06a494bf6ac544d70458fb12d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732626B2

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