Ethyl bromoacetate → (+/-) Ethyl 2-(1-hydroxy-1,2,3,4-tetrahydro-4,4-dimethyl-7-bromo-naphthalen-1-yl)acetate

HRID 611046

Reaktionsgleichung

Reaktionsgleichung von HRID 611046
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15][C:16]2=[O:19])=[CH:11][CH:10]=1>C1C=CC=CC=1.[Zn]>[OH:19][C:16]1([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([Br:8])[CH:18]=2)[C:13]([CH3:21])([CH3:20])[CH2:14][CH2:15]1

Komponenten

5

Edukt 2

HCID 7748Ethyl bromoacetateHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×

Produkt 1

HCID 22571522(+/-) Ethyl 2-(1-hydroxy-1,2,3,4-tetrahydro-4,4-dimethyl-7-bromo-naphthalen-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To a suspension of Zn (1.20 g, 18.4 mmol) in 10 mL benzene at 100° C. was slowly added a solution of ethyl 2-bromoacetate (658.0 mg, 3.94 mmol) and 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G, 500.0 mg, 1.97 mmol) in 20.0 mL benzene. The resulting mixture was heated for 2 h, cooled to room temperature, and the solution decanted from the residual solids. The solids were washed with EtOAc and the combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes) afforded the title compound as a yellow oil.

Aufarbeitung

  1. temperatureThe resulting mixture was heated for 2 h
  2. customthe solution decanted from the residual solids
  3. washThe solids were washed with EtOAc
  4. washthe combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl
  5. dry with materialbefore being dried over MgSO4
  6. customRemoval of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-002e61c18f59491182e888987900781b
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998655

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