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Sodium borohydride → Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422306
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2422306
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1)=[O:2].[BH4-].[Na+]>CO.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1
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Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 23082902HCID 23082902, Verbindung

Produkt 1

HCID 23082953Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl 3-(4-(2′-formylbiphenyl-3-ylmethoxy)phenyl)propanoate (0.30 g, 0.72 mmol) was dissolved in a mixed solution of methanol (6 mL) and tetrahydrofuran (6 mL), and sodium borohydride (14 mg, 0.36 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1) to give the title compound (0.25 g, yield 83%) as a colorless oil.

Aufarbeitung

  1. additionwas added under ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with 1N hydrochloric acid and saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1)

Quellen und Nachweise

ORD-Eintrag
ord-826d0074c7cd46fab6c3342b40a67b53
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07960369B2

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