Perchloric Acid → 3-((tert-Butyldiphenylsilyl)oxy)cyclobutanone

HRID 1426281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426281
[C:1]([Si:5]([O:18][CH:19]1[CH2:22][C:21](S(C)=O)(SC)[CH2:20]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl(O)(=O)(=O)=[O:29]>CCOCC.O>[Si:5]([O:18][CH:19]1[CH2:22][C:21](=[O:29])[CH2:20]1)([C:1]([CH3:3])([CH3:4])[CH3:2])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 2

HCID 24247Perchloric AcidHCID 86666495Tert-butyl{[3-(methylsulfinyl)-3-(methylthio)cyclobutyl]oxy}diphenylsilane

Produkt 1

HCID 668245053-((tert-Butyldiphenylsilyl)oxy)cyclobutanoneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of tert-butyl{[3-(methylsulfinyl)-3-(methylthio)cyclobutyl]oxy}diphenylsilane (17.05 g, 40.7 mmol, from Step 2) in ether (350 mL) cooled to 0° C. was treated with a solution of 6M perchloric acid in water (10 mL) that was pre-diluted with water (7 mL). The bath was removed and stirred overnight. The mixture was poured into pH 7 buffer, and the product was extracted with diethyl ether. The combined extracts were dried over sodium sulfate, decanted and concentrated. The reaction was performed again on the same scale and the two batches were combined for purification. Flash chromatography, eluting with a gradient from 0-5% ethyl acetate/hexanes afforded desired product (15.7 g, 59%). 1H NMR (300 MHz, CDCl3): δ 7.75-7.62 (m, 4H), 7.49-7.33 (m, 6H), 4.59 (tt, 1H), 3.22-3.03 (m, 4H), 1.07 (s, 9H).

Aufarbeitung

  1. customThe bath was removed
  2. additionThe mixture was poured into pH 7 buffer
  3. extractionthe product was extracted with diethyl ether
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. customthe two batches were combined for purification
  8. washFlash chromatography, eluting with a gradient from 0-5% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2c446867334f4a09acf74ea295a4e3c9
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

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