1,4-Dioxaspiro[4.5]decan-8-one → 8-Methylidene-1,4-dioxaspiro[4.5]decane

HRID 252027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252027
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]1[C:10]2(CCC(=O)[CH2:12][CH2:11]2)[O:9][CH2:8][CH2:7]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:4]=[C:3]1[CH2:12][CH2:11][C:10]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:1][CH2:2]1

Komponenten

5

Edukt 2

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Produkt 1

HCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decaneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To solution of methyltriphenylphosphonium bromide (17 g, 1.5 eq.) in THF (100 mL) at 0° C. was added dropwise n-butyllithium (2.5 M in hexanes, 18 mL, 1.4 eq.) and the resulting mixture was stirred for 1 h. A solution of 1,4-dioxa-spiro[4.5]decan-8-one (5.0 g, 32 mmol, 1.0 eq.) in THF (10 mL) was then introduced dropwise and the resulting mixture was warmed to room temperature and stirred overnight. The reaction was quenched by addition of sat. NaHCO3 and the separated aqueous layer was extracted with 4×EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography (5% to 10% EtOAc/hexanes) to give 8-methyene-1,4-dioxa-spiro[4.5]decane (3.92 g, 79%).

Aufarbeitung

  1. stirringstirred overnight
  2. customThe reaction was quenched by addition of sat. NaHCO3
  3. extractionthe separated aqueous layer was extracted with 4×EtOAc
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (5% to 10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-058feca66c504484af53b584355b3362
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868002B2

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