Methanol → 5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

HRID 2244907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244907
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([OH:12])[CH2:7][CH2:6]2

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 121749875-(Trifluoromethyl)indan-1-one

Produkt 1

HCID 248204735-(trifluoromethyl)-2,3-dihydro-1H-inden-1-olAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-(trifluoromethyl)indan-1-one (0.7 g, 3 mmol) in THF (5 mL) cooled in an ice bath was added sodium borohydride (0.1 g, 3 mmol) followed by MeOH (1 mL). After being stirred for 30 min, the reaction was quenched with aqueous NaHCO3. The resulting solution was extracted with EtOAc twice. The extracts were washed with brine, dried (MgSO4), filtered and, concentrated. The crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane to afford the desired product (0.65 g, 92%) as an oil. LC/MS calculated for C10H9F3O: (M+H)+ 203; found 185.1 (M+H—H2O)+.

Aufarbeitung

  1. customthe reaction was quenched with aqueous NaHCO3
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica eluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-42a33bca6e93498eacb2edf6ccb39bb3
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678798B2

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