Reaction #53612

Reaction equation

Sodium hydride

compound ( 33 )

2,9-Dihydro-6-oxa-2-azabenzo[cd]azulen-8-one ethylene ketal

benzenesulfonyl chloride

→

titled compound ( 34 )

Yield 69.0%

2-Benzenesulfonyl-2,9-dihydro-6-oxa-2-azabenzo[cd]azulen-8-one ethylene ketal

Yield 69.0%

Solvents

dimethylformamide

chloroform hexane

Conditions

Workup

1. 1
   Temperaturewith cooling in ice
2. 2
   Extractionwas extracted with ethyl acetate
3. 3
   WashThe extracts were washed with brine
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe residue obtained

Procedure

60% Sodium hydride 33 mg was added to a solution of compound (33) in dry dimethylformamide 2 ml with cooling in ice and the mixture was stirred for 10 min. Then, benzenesulfonyl chloride 152 mg was added. The mixture was heated at 60° C. for 14 h. Ice-water was added to the reaction mixtures, which was extracted with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was choromatographed on aluminum oxide in chloroform:hexane (1:1) to give the titled compound (34) as a pale yellow oil, 187 mg. Yield 69%.

Source