Diisopropylethylamine → 3-(tert-Butyldimethylsilyloxy)cyclobutyl pivalate

HRID 1039690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039690
[C:1]([O:7][CH:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CCN(C(C)C)C(C)C.O([Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[C:1]([O:7][CH:8]1[CH2:9][CH:10]([O:12][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:11]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 575158713-Hydroxycyclobutyl 2,2-dimethylpropanoate

Produkt 1

HCID 575158723-(tert-Butyldimethylsilyloxy)cyclobutyl pivalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 3-hydroxycyclobutyl pivalate (16.60 g, 96.4 mmol) and diea (25.2 ml, 145 mmol) in DCM (100 ml) at 0° C. was added tert-butyldimethylsilyl triflate (31.0 ml, 135 mmol) dropwise. The reaction was stirred for 2 h, then quenched with H2O. The layers were separated, and the organic layer was washed with saturated NaHCO3, brine, dried over MgSO4 and concentrated to give the title compound as a light brown oil.

Aufarbeitung

  1. customquenched with H2O
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ce1e436368494aedbfc2a28bc93967f6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552181B2

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