Toluene → Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-7-yl]naphth-2-oate

HRID 1599875

Reaktionsgleichung

Reaktionsgleichung von HRID 1599875
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](C(OCC)=O)=[CH:7][CH:6]=[CH:5]2.[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+].[CH3:23][C:24]1([CH3:45])[CH2:33][CH2:32][CH:31]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C:30]2[CH:29]=[C:28](B(O)O)[CH:27]=[CH:26][C:25]1=2.[C:46]1(C)C=CC=C[CH:47]=1>CO>[CH2:46]([O:18][C:17]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:32]3[CH:31]([O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36])[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:24]([CH3:23])([CH3:45])[CH2:33]3)[CH:3]=2)[CH:8]=1)=[O:20])[CH3:47]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 22571499(5,6,7,8-Tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acidHCID 22571542Ethyl 6-bromo-1-naphthoate

Produkt 1

HCID 22571555Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-7-yl]naphth-2-oate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a degassed solution of 722 mg (2.6 mmol) of ethyl 6-bromonaphthalenecarboxylate in 6.0 mL of toluene, was added sequentially 90 mg (0.08 mmol) of tetrakis-triphenylphosphine palladium (O), 5.0 mL (10.0 mmol) of 2M sodium carbonate, and a solution of 1.018 g (3.1 mmol) of (5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acid (Compound B14) in 3.0 mL of MeOH. The reaction was heated at 90° C. for 15 h. The reaction was diluted with 2N Na2 CO3, and extracted with CH2Cl2 (2×), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. The crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane) to afford the title compound as a white solid.

Aufarbeitung

  1. additionThe reaction was diluted with 2N Na2 CO3
  2. extractionextracted with CH2Cl2 (2×)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d4dde5758b184bf4bd54c142801c2c11
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05741896

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