2,6-Lutidine → [4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic Acid

HRID 2282013

Reaktionsgleichung

Reaktionsgleichung von HRID 2282013
C[O:2][P:3]([CH2:7][C:8]([CH3:25])=[CH:9][CH2:10][C:11]1[C:12]([OH:24])=[C:13]2[C:17](=[C:18]([CH3:22])[C:19]=1[O:20][CH3:21])[CH2:16][O:15][C:14]2=[O:23])(=[O:6])[O:4]C.C[Si](Br)(C)C.N1C(C)=CC=CC=1C>C(#N)C>[OH:24][C:12]1[C:11]([CH2:10][CH:9]=[C:8]([CH3:25])[CH2:7][P:3](=[O:2])([OH:6])[OH:4])=[C:19]([O:20][CH3:21])[C:18]([CH3:22])=[C:17]2[C:13]=1[C:14](=[O:23])[O:15][CH2:16]2

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 76113BromotrimethylsilaneHCID 75023209[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic Acid Dimethyl Ester

Produkt 1

HCID 67010405[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic AcidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of [4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic acid dimethyl ester (18 mg, 0.049 mmol) in acetonitrile (2 mL) was added TMSBr (63 μL, 0.49 mmol) and 2,6-lutidine (85 μL, 0.73 mmol) at 0° C. The reaction solution was allowed to warm to room temperature and stirred for 2 hours when completion of the reaction was observed by LCMS. The reaction was cooled to 0° C. and quenched by the addition of MeOH. The reaction mixture was concentrated under reduced pressure and the residue was purified by RP HPLC using a C18 column with a gradient of H2O-acetonitrile (5-0%) over 20 minutes to provide 12.2 mg (73%) of the product. 1H NMR (300 MHz, CD3OD) δ 1.95 (s, 3H), 2.15 (s, 3H), 2.48 (d, 2H, J=22 Hz), 3.44 (t, 2H, J=6 Hz), 3.79 (s, 3H), 5.24 (s, 2H), 5.38 (q, 1H, J=7 Hz), 6.87 (br s, 1H) ppm; MS (m/z) 341 [M−H]−.

Aufarbeitung

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched by the addition of MeOH
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by RP HPLC
  5. customover 20 minutes

Quellen und Nachweise

ORD-Eintrag
ord-350b79a42bf64f729b6192c4e222eac1
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139604B2

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