Potassium Hydroxide → Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate

HRID 384077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384077
[OH-].[K+].[O:3]1[CH2:6][C:5](=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1.[Br:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1>O1CCOCC1.[Cl-].[Na+].O>[Br:13][C:14]1[CH:19]=[C:18]([C:5]2([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][O:3][CH2:4]2)[CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 2734318(3-Bromophenyl)boronic acid2×HCID 53308471Ethyl 2-(oxetan-3-ylidene)acetate

Produkt 1

HCID 57969689Ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 312751,4-DioxaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of [Rh(cod)C1]2 (171.3 mg, 0.3518 mmol) in 30 mL of dioxane was added aqueous KOH (6.097 mL of 1.5 M, 9.145 mmol) followed by ethyl 2-(oxetan-3-ylidene)acetate (1 g, 7.035 mmol) and a solution of (3-bromophenyl)boronic acid (2.119 g, 10.55 mmol) in 10 mL of dioxane. The reaction was stirred for 30 minutes at room temperature then further (3-bromophenyl)boronic acid (706 mg, 0.5 eq) was added and the reaction stirred overnight. Brine was added and the aqueous layer extracted twice with ethyl acetate. The combined organics were washed with brine and then dried, filtered and concentrated under reduced pressure. The crude product was purified on silica (Companion, 80 g) eluting with 1-20% EtOAc:Petrol ether to give ethyl 2-[3-(3-bromophenyl)oxetan-3-yl]acetate as a yellow oil (1.50 g, 71%).

Aufarbeitung

  1. stirringthe reaction stirred overnight
  2. extractionthe aqueous layer extracted twice with ethyl acetate
  3. washThe combined organics were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified on silica (Companion, 80 g)
  8. washeluting with 1-20% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-4440f4e92bb444bba2e696875d2d0acf
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367697B2

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