Diisopropyl bromomethylphosphonate → {2-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilany-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-ethoxymethyl}-phosphonic Acid Diisopropyl Ester

HRID 32970

Reaktionsgleichung

Reaktionsgleichung von HRID 32970
[OH:1][CH2:2][CH2:3][C:4]1[C:12]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:20])=[C:6]([CH3:21])[C:5]=1[O:22][CH3:23].[CH:24]([O:27][P:28]([CH2:34]Br)(=[O:33])[O:29][CH:30]([CH3:32])[CH3:31])([CH3:26])[CH3:25].CC(C)([O-])C.[Li+]>CN(C=O)C>[CH:30]([O:29][P:28]([CH2:34][O:1][CH2:2][CH2:3][C:4]1[C:12]([O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])=[C:11]2[C:7](=[C:6]([CH3:21])[C:5]=1[O:22][CH3:23])[CH2:8][O:9][C:10]2=[O:20])(=[O:33])[O:27][CH:24]([CH3:26])[CH3:25])([CH3:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 4366885Diisopropyl bromomethylphosphonateHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 574598516-(2-Hydroxy-ethyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

Produkt 1

HCID 57478687{2-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilany-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-ethoxymethyl}-phosphonic Acid Diisopropyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6-(2-hydroxy-ethyl)-5-methoxy-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (79 mg, 0.23 mmol) was heated with bromomethylphosphonic acid diisopropyl ester (120 mg, 0.46 mmol) in the presence of lithium t-butoxide (22 mg, 0.27 mmol) in DMF (2 mL) at 70° C. overnight. The reaction mixture was purified by RP HPLC (acetonitrile and 0.1% aqueous CF3COOH) to provide the desired product. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 1.13-1.25 (m, 2H), 1.26 (t, 12H, J=6 Hz), 2.12 (s, 3H), 2.98 (t, 2H, J=7 Hz), 3.60-3.73 (m, 4H), 3.77 (s, 3H), 4.05-4.16 (m, 2H), 4.62-4.74 (m, 2H), 5.07 (s, 2H) ppm; MS (m/z) 539 [M+Na]+.

Aufarbeitung

  1. customThe reaction mixture was purified by RP HPLC (acetonitrile and 0.1% aqueous CF3COOH)

Quellen und Nachweise

ORD-Eintrag
ord-82327874a61b4984839a6e402c5c2154
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427636B2

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