Ethyl acetate hexane → 2-(1-((Tert-butyldimethylsilyl)oxy)cyclobutyl)acetaldehyde

HRID 253139

Reaktionsgleichung

Reaktionsgleichung von HRID 253139
[Si:1]([O:8][C:9]1([CH2:13][CH:14]([OH:17])CO)[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1.CC(O)(C)C.O.I([O-])(=O)(=O)=O.[Na+].CCOC(C)=O.CCCCCC>O>[Si:1]([O:8][C:9]1([CH2:13][CH:14]=[O:17])[CH2:10][CH2:11][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 21226206Ethyl acetate hexaneHCID 22124471t-Butanol tetrahydrofuran waterHCID 23667635Sodium periodateHCID 668451483-(1-(Tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol

Produkt 1

HCID 866140212-(1-((Tert-butyldimethylsilyl)oxy)cyclobutyl)acetaldehydeAusbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 2 L round bottomed flask was added 3-(1-(tert-butyldimethylsilyloxy)cyclobutyl)propane-1,2-diol (80.0 g, 307 mmol) and THF/t-BuOH/H2O (1:1:2, 2 L). Sodium periodate (120.15 g, 562 mmol) was added and the reaction was stirred at RT. After addition the solution became yellow and thickened. The stirrer was adjusted to maintain stirring. After 1.5 h, the reaction is complete as monitored by TLC (10% EtOAc/Hexane). 300 mL H2O was added to the reaction and the aqueous solution was extracted with ether (3×600 mL). The combined organics were dried over MgSO4 and carefully concentrated in vacuo (Note: volatile product). The oil was re-dissolved in 200 mL of benzene and azeotroped to remove any excess t-BuOH. The crude oil was adsorbed onto a plug of silica gel and chromatographed through a glass column, eluting with 3% EtOAc in hexane, to provide a golden oil after concentrating in vacuo (Note: volatile product). The oil was dissolved in 200 mL of benzene and concentrated in vacuo. The mixture was further concentrated to remove excess benzene to give 2-(1-(tert-butyldimethylsilyloxy)cyclobutyl) acetaldehyde (67.5 g, 296 mmol, 96.2% yield). The title compound yielded contained some benzene and was carried forward without further purification.

Aufarbeitung

  1. additionAfter addition the solution
  2. temperatureto maintain
  3. stirringstirring
  4. extractionthe aqueous solution was extracted with ether (3×600 mL)
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationcarefully concentrated in vacuo (Note: volatile product)
  7. dissolutionThe oil was re-dissolved in 200 mL of benzene
  8. customazeotroped
  9. customto remove any excess t-BuOH
  10. customchromatographed through a glass column
  11. washeluting with 3% EtOAc in hexane
  12. customto provide a golden oil
  13. concentrationafter concentrating in vacuo (Note: volatile product)
  14. dissolutionThe oil was dissolved in 200 mL of benzene
  15. concentrationconcentrated in vacuo
  16. concentrationThe mixture was further concentrated
  17. customto remove excess benzene

Quellen und Nachweise

ORD-Eintrag
ord-d926233670294b70bfc634a07920f03d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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