Reaction #1833260

Reaction equation

Acryloyl chloride

C3-hydroxy β-lactam

3-Hydroxy-N-(4-methoxyphenyl)-4-(2-chloro phenyl)-2-azetidinone

NaH

→

25

Yield 75.4%

3-acryloyl-N-(4-methoxyphenyl)-4-(2-chlorophenyl)-2-azetidinone

Yield 75.4%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe reaction was quenched with a 5% solution of NH4Cl
2. 2
   Extractionextracted (3×20 ml) with CH2Cl2
3. 3
   DryingThe combined organic layers were dried over anhydrous MgSO4
4. 4
   Otherpurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

Procedure

To a solution of C3-hydroxy β-lactam 24 (5.80 g, 19.1 mmol) in 30 ml of freshly distilled CH2Cl2 was added NaH (60% suspension in mineral oil, 0.83 g, 21.0 mmol), and the mixture was stirred for 15 min at room temperature. Acryloyl chloride (2.59 g, 28.64 mmol) was then added dropwise and the resultant mixture was stirred until TLC indicated the disappearance of starting material. The reaction was quenched with a 5% solution of NH4Cl and extracted (3×20 ml) with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 4.92 g (72%) of 25 as a white solid, mp 99-100° C. 1H NMR (250 MHz) δ 7.33 (d, J=7.9 Hz, 1H), 7.23-7.10 (m, 5H), 6.75 (d, J=8.9 Hz, 2H), 6.17 (d, J=5.0 Hz, 1H), 5.98 (dd, J=16.9, 1.00 Hz, 1H), 5.74 (dd, J=16.9, 10.4 Hz, 1H), 5.69 (d, J=5.0 Hz, 1H), 5.59 (d, J=10.4, 1.0 Hz, 1H), 3.66 (s, 3H). 13C NMR (63 MHz) δ 163.6, 161.2, 156.6, 133.7, 132.3, 130.3, 130.1, 129.8, 128.5, 126.8, 126.5, 118.6, 114.4, 75.3, 61.3, 58.2, 55.3.

Source