Water → Spiro[3.5]nonan-2-one

HRID 1853076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853076
Cl[C:2]1(Cl)[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:11].O>C(O)(=O)C.[Zn]>[CH2:2]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]1=[O:11]

Komponenten

5

Edukt 2

HCID 962WaterHCID 156384721,1-Dichlorospiro[3.5]nonan-2-one

Produkt 1

HCID 58227859Spiro[3.5]nonan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

According to a literature procedure (Tetrahedron 1993, 49(36), 8159). A mixture of 1,1-dichlorospiro[3.5]nonan-2-one (5.00 g; 24.1 mmol) and zinc dust (4.74 g; 72.4 mmol) was stirred in acetic acid (60 mL) and water (30 mL) for 4 hours. The solution was then stored at −20° C. for 15 hours. The mixture was filtered through Celite®, washing with ether and hexane, and then the filtrate was washed with aqueous sodium hydroxide solution (2N; 4×100 mL). (This resulted in the precipitation of white salts, which needed to be removed by filtration). The organic phase was washed with water (30 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure. The material was purified by chromatography on silica gel, eluting with hexane/ether (10:1) to give the desired product as an almost colorless oil (2.56 g).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite®
  2. washwashing with ether and hexane
  3. washthe filtrate was washed with aqueous sodium hydroxide solution (2N; 4×100 mL)
  4. custom(This resulted in the precipitation of white salts, which
  5. customto be removed by filtration)
  6. washThe organic phase was washed with water (30 mL)
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe material was purified by chromatography on silica gel
  11. washeluting with hexane/ether (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-987d453f53394426beb7cc639c35cccb
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

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