Acetic Acid → HCID 10704760, Verbindung

HRID 1700956Notizen

Reaktionsgleichung

C[Li].[Si:3]([O:10][C@H:11]1[CH2:16][CH2:15][O:14][C:12]1=[O:13])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[C:17](O)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)C.C1COCC1>[Si:3]([O:10][C@H:11]1[CH2:16][CH2:15][O:14][C:12]1([OH:13])[CH3:17])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Methyl lithium (670 μl [1.11 mmol, 1.1 equiv] of a 1.65 M solution in diethyl ether) is added dropwise to a stirred solution of (S)-2-(tertbutyidimethylsilyloxy)-γ-butyrolactone 12 (218 mg, 1.01 mmol) in THF (4.0 ml) cooled to −78° C. is added dropwise. After stirring at −78° C. for 3 h, the reaction is quenched by the addition of glacial acetic acid (72 μl, 1.26 mmol, 1.25 equiv). Diethyl ether (20 ml) and saturated aqueous sodium bicarbonate solution (10 ml) are added. After stirring for 5 min the organic layer is separated and the aqueous layer is extracted with diethyl ether (2×20 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacua. Crude (3S)-3-(tertbutyidimethylsilyloxy)-2-hydroxy-2-methyl-tetrahydrofurane 13 (235 mg, 93%) is obtained as a colourless crystalline solid (mixture of diastereomers) which is used for the synthesis of (S)-3,5-di-(tert-butyldimethylsilyloxy)-pentan-2-one 14 without further purification.

Aufarbeitung

additionis added dropwise
stirringAfter stirring for 5 min the organic layer
customis separated
extractionthe aqueous layer is extracted with diethyl ether (2×20 ml)
dry with materialThe combined organic extracts are dried over magnesium sulfate
concentrationconcentrated in vacua

Quellen und Nachweise

ORD-Eintrag: ord-5ea315a495474b1492ddbfbd23634523
Quelldatensatz: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06350878B1

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