Potassium Carbonate → HCID 23353989, compound

HRID 235274Notes

Reaction equation

HRID 235274 reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1[S:28][C:11]2[CH2:12][CH2:13][CH:14]3[C:19]([C:10]=2[CH:9]=1)=[N:18][N:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[C:16](=[O:27])[CH2:15]3)=O)(=[O:3])[CH3:2].C([SiH](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][CH2:6][C:8]1[S:28][C:11]2[CH2:12][CH2:13][CH:14]3[C:19]([C:10]=2[CH:9]=1)=[N:18][N:17]([C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[C:16](=[O:27])[CH2:15]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 23353990HCID 23353990, compound

Product 1

HCID 23353989HCID 23353989, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 3 g of 8-acetoxyacetyl-4,4a,5,6-tetrahydro-2-(4methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in 30 ml of trifluoroacetic acid was added 2.7 ml of triethylsilane and the mixture was stirred at room temperature for 24 hours. The mixture was poured into ice-cold water, neutrallized with potassium carbonate and then extracted with chloroform. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :100 g) column using chloroform as an eluent. The resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane to give 2.0 g of 8-(2-acetoxyethyl)-4,4a,5,6-tetrahydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a white powder, melting at 73°-75° C.

Workup

  1. additionThe mixture was poured into ice-cold water
  2. extractionextracted with chloroform
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on a silica gel (SiO2 :100 g) column
  7. customThe resulting solid was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c162fa2ab98d4489ba93a6dd89a9f4b4
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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