Cerium(III) chloride → 4-Hydroxycyclohex-1-ene-1-carbonitrile

HRID 521199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521199
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:8]#[N:9])=[CH:4][CH2:3]1.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO.O>[OH:1][CH:2]1[CH2:7][CH2:6][C:5]([C:8]#[N:9])=[CH:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 189737114-Oxocyclohex-1-ene-1-carbonitrile

Produkt 1

HCID 867293624-Hydroxycyclohex-1-ene-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-oxocyclohex-1-ene-1-carbonitrile (170 mg, 1.40 mmol) in MeOH (2.3 mL) at −78° C. was added cerium (III) chloride (484 mg, 1.96 mmol) in MeOH (4.7 mL). The resulting mixture was allowed to stir for 5 minutes at −78° C. before NaBH4 (48 mg, 1.26 mmol) was added in one portion. The mixture was stirred for 20 minutes and then allowed to warm to ambient temperature. After being stirred for 30 minutes, the reaction mixture was diluted with water and extracted with diethyl ether (3×). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo (23° C. water bath) to afford the title compound.

Aufarbeitung

  1. additionwas added in one portion
  2. stirringAfter being stirred for 30 minutes
  3. extractionextracted with diethyl ether (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo (23° C. water bath)

Quellen und Nachweise

ORD-Eintrag
ord-419dd61cae4f4fa59c2c2483768aad5d
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328099B2

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