Triphenylphosphine → 6-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-one

HRID 272196

Reaktionsgleichung

Reaktionsgleichung von HRID 272196
[CH2:1]([C:4]1[C:12]([OH:13])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:37][Si:38]([CH3:43])([CH3:42])[CH2:39][CH2:40]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:1]([C:4]1[C:12]([O:13][CH2:40][CH2:39][Si:38]([CH3:43])([CH3:42])[CH3:37])=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:14])=[C:6]([CH3:15])[C:5]=1[CH2:16][CH3:17])[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 180132-(Trimethylsilyl)ethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 574598626-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one

Produkt 1

HCID 574598636-Allyl-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)3H-isobenzofuran-1-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-allyl-5-ethyl-7-hydroxy-4-methyl-3H-isobenzofuran-1-one (199 mg, 0.857 mmol), PPh3 (337 mg, 1.286 mmol), and 2-trimethylsilylethanol in THF (3 mL) at 0° C. was added diisopropyl azodicarboxylate (259 mg, 1.286 mmol). The resulting yellow solution was allowed to warm to room temperature and stirred for one hour. The solvent was removed in vacuo and the crude material was dissolved in diethyl ether (3 mL). Hexanes (1.5 mL) were added. Triphenylphosphine oxide was removed by filtration and the filtrate was concentrated and purified by silica gel chromatography to provide the desired product (261 mg, 92%) as a clear oil. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.25 (m, 2H), 2.20 (s, 3H), 2.73 (q, J=7.8 Hz, 2H), 3.54 (m, 2H), 4.28 (m, 2H), 4.95 (d, J=17.1 Hz, 1H), 5.02 (d, J=10.2 Hz, 1H), 5.15 (s, 2H), 5.95 (m, 1H) ppm.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude material was dissolved in diethyl ether (3 mL)
  3. additionHexanes (1.5 mL) were added
  4. customTriphenylphosphine oxide was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-73a2fce80a0840128c8bc3b020a3d5ae
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452901B2

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