Ethyl Acetate → {4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl Ester

HRID 33018

Reaktionsgleichung

Reaktionsgleichung von HRID 33018
[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:16])[O:9]C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CCOC(C)=O>C1COCC1>[C:1]1([O:7][P:8]([CH2:17][C:18]([CH3:41])=[CH:19][CH2:20][C:21]2[C:22]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:38])[CH3:39])=[C:23]3[C:27](=[C:28]([CH3:32])[C:29]=2[O:30][CH3:31])[CH2:26][O:25][C:24]3=[O:33])(=[O:9])[OH:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 76546201{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Diphenyl Ester

Produkt 1

HCID 76548829{4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic Acid Monophenyl EsterAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of {4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}-phosphonic acid diphenyl ester (75 mg, 0.126 mmol) in THF (5 mL) was added 1N NaOH (0.1 mL) solution. The mixture was allowed to stir at room temperature for 16 hours. EtOAc was added and the resulting mixture was washed with 1H HCl. The organic layer was concentrated to dryness and the residue was purified by RP HPLC using a C18 column with a gradient of H2O, 0.1% TFA-acetonitrile, 0.1% TFA to provide 24.8 mg (38%) of the desired product. MS (m/z) 517 [M−H]−, 541 [M+Na]+.

Aufarbeitung

  1. washthe resulting mixture was washed with 1H HCl
  2. concentrationThe organic layer was concentrated to dryness
  3. customthe residue was purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8fc348197f2043faad1824a0f62a203f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427636B2

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