Ammonium Chloride → Tert-butyl 3-chloro-4-(3-hydroxycyclohexyl)benzoate

HRID 1849763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1849763
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Na].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 86703645Tert-butyl 3-chloro-4-(3-oxocyclohexyl)benzoate

Produkt 1

HCID 86703646Tert-butyl 3-chloro-4-(3-hydroxycyclohexyl)benzoateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of tert-butyl 3-chloro-4-(3-oxocyclohexyl)benzoate in anhydrous methanol (50 mL) was added sodium borobydride (1.04 g, 27.40 mmol) at 0° C. The reaction mixture was stirred for 1 hour at 0° C., after which saturated ammonium chloride solution (10 mL) was added. All volatiles were evaporated under reduced pressure, and the residue was partitioned between ethyl acetate (200 mL) and water (20 mL). The organic phase was washed with brine (10 mL), dried over sodium sulfate, and filtered. Concentration under reduced pressure gave a residue which was purified by silica gel column chromatography using 0-40% ethyl acetate in hexanes as eluent to afford the title compound as colorless oil (2.24 g, 53%): 1H NMR (300 MHz, CDCl3) δ 7.94-7.92 (m, 1H), 7.84-7.79 (m, 1H), 7.32-7.27 (m, 1H), 3.85-3.69 (m, 1H), 3.16-3.03 (m, 1H), 2.19-2.04 (m, 2H), 1.96-1.77 (m, 2H), 1.63-1.18 (m, 14H); MS (ES+) m/z 255.2, 257.1 (M−55).

Aufarbeitung

  1. customAll volatiles were evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (200 mL) and water (20 mL)
  3. washThe organic phase was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under reduced pressure
  7. customgave a residue which
  8. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d314e415009d49d2ba5b6c004fdc9f4a
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952169B2

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