Sodium Chloride → 3-Oxo-2,3-dihydro[1]benzothiophene-2-spirocyclopropane

HRID 1659546

Reaction equation

HRID 1659546 reaction equation
O1[CH2:5][CH2:4][C:3]2([S:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]2=[O:14])C1=O.[Cl-].[Na+]>CS(C)=O>[O:14]=[C:6]1[C:3]2([CH2:4][CH2:5]2)[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]1=2

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 136222834',5'-dihydrospiro[benzo[b]thiophene-2(3H), 3'(2'H)-furan]3,2'-dione

Product 1

HCID 123940523-Oxo-2,3-dihydro[1]benzothiophene-2-spirocyclopropaneYield 81.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 8.0 g of 4',5'-dihydrospiro[benzo[b]-thiophene-2(3H),3'(2'H)-furan]-3,2'-dione, 2.3 g of sodium chloride and 20 ml of dimethylsulfoxide is stirred in nitrogen streams at 155°-160° C. for 3.5 hours. The reaction mixture is poured in ice-water, the resultant precipitate recovered by filtration and rinsed, and the residue recrystallized from methanol. By the above procedure there is obtained 5.2 g of 3-oxo-2,3-dihydro[1]benzothiophene-2-spirocyclopropane as colorless platelets melting at 70° C.

Workup

  1. filtrationthe resultant precipitate recovered by filtration
  2. washrinsed
  3. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-7d54bf6ab2674a739b3dcdd6e3993ae4
Source dataset
uspto-grants-1981_12
Patent number
US04304784

Linked notes

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