Benzcatechinborane → Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

HRID 926152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926152
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:26])[C:8]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[B]1OC2C(=CC=CC=2)O1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:26])[C:8]([CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]2[C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6327445BenzcatechinboraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 67126218Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

Produkt 1

HCID 67126259Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate (1.6 g, 2.78 mmol) and (R)-2-methyl-CBS-oxazaborolidine (116 mg, 0.42 mmol) in anhydrous toluene at −40° C. was added a solution of catecholborane (355 μL, 3.34 mmol) in toluene (1.6 mL) over 15 minutes. The reaction mixture was stirred for 1 hour and quenched with sodium carbonate solution, diluted with ethyl acetate and stirred vigorously for 20 minutes at room temperature. The aqueous layer was removed and the organic layer was washed with sodium carbonate solution (4×), saturated ammonium chloride solution, dried, filtered, concentrated in vacuo and purified by flash column chromatography to give the desired product.

Aufarbeitung

  1. customquenched with sodium carbonate solution
  2. additiondiluted with ethyl acetate
  3. stirringstirred vigorously for 20 minutes at room temperature
  4. customThe aqueous layer was removed
  5. washthe organic layer was washed with sodium carbonate solution (4×), saturated ammonium chloride solution
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4504d7d86a1e4c4e935c7feb36d4d002
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284323B2

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