Sulfuric acid magnesium salt (1:1) → 1-(t-Butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone
Reaction equation
[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]=[O:14])[CH2:10][C:9]1=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][Mg+].[Br-].[O-]S([O-])(=O)=O.[Mg+2]>CCOCC>[Si:1]([N:8]1[CH:11]([CH2:12][CH:13]([OH:14])[CH3:16])[CH2:10][C:9]1=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
1-(t-butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone (2.27 g, 0.01 mole) is dissolved in 50 ml ether and cooled to -20° C. under N2. A solution of CH3MgBr in ether (0.011 mole CH3MgBr) is added dropwise over 1/2 hours at -20° C. and the reaction mixture is stirred for another 1/2 hr at -20°, allowing to rise to 25° C. The reaction mixture is treated with a saturated solution of MgSO4 (2 ml) and allowed to stir for 15 min. The Mg salts are filtered off and washed with ether. The combined filtrate and washings are dried and evaporated. Chromatography of the residue on silica gel gives 1-(t-butyldimethylsilyl)-4-(2-hydroxypropyl)-2-azetidinone.
Workup
- customto rise to 25° C
- stirringto stir for 15 min
- filtrationThe Mg salts are filtered off
- washwashed with ether
- customThe combined filtrate and washings are dried
- customevaporated
Sources & evidence
- ORD record
- ord-8ac9d759f6234063866ba7e95e250305
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775669
Reaction notes
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