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

HRID 717865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717865
[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 6 M 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-e9eea22c45ae487ebb3b1daeed44ca54
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193733B2

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