1-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone → 2-Azetidinone

HRID 1702572Notes

Reaction equation

HRID 1702572 reaction equation
[Si]([N:8]1[CH:11](CC=O)[CH2:10][C:9]1=[O:15])(C(C)(C)C)(C)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([Mg:24][Br:25])=[CH:20][CH:19]=1>CCOCC>[NH:8]1[CH2:11][CH2:10][C:9]1=[O:15].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([Mg:24][Br:25])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 128047181-(t-Butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinoneHCID 178491912HCID 178491912, compound

Product 2

HCID 1367212-AzetidinoneHCID 178491912HCID 178491912, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Treatment of 1-(t-butyldimethylsilyl)-4-(2-oxoethyl)-2-azetidinone (0.01 mole) with p-methoxyphenyl-magnesium bromide (1.1 eq.; in ether at 0° C. gives 2-azetidinone with p-methoxyphenyl-magnesium bromide gives 1-(t-butyl dimethylsilyl)-4-(2-hydroxyethyl-2-p-methoxyphenyl)-2-azetidinone which is acetylated as described before (Ex. 3, Step C) to give 4-(2-acetoxy-2-p-methoxyphenyl)-2-azetidinone.

Sources & evidence

ORD record
ord-4fb70e7df10b49e493f0dfc805253f72
Source dataset
uspto-grants-1982_09
Patent number
US04348320

Reaction notes

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