Hydrochloric Acid → 4-(3-Furyl)-7-mercaptocoumarin

HRID 260447Notes

Reaction equation

HRID 260447 reaction equation
C[Si](C)(C)CC[S:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:17]3[CH:21]=[CH:20][O:19][CH:18]=3)=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].Cl>CN(C=O)C.C1COCC1.O>[SH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([C:17]3[CH:21]=[CH:20][O:19][CH:18]=3)=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 233702447-(2-Trimethylsilylethylthio)-4-(3-furyl)coumarin

Product 1

HCID 233701944-(3-Furyl)-7-mercaptocoumarinYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The coumarin from Step 1 (963 mg) was dissolved in DMF (25 mL) and to this solution there was added n-Bu4NF (1M) in THF (8.4 mL). The mixture was stirred at r.t. for 2 h, poured onto 1N aqueous HCl (50 mL), diluted with H2O (50mL) and filtered to afford the title compound (620 mg) as a tan. solid. m.p.: 167°-170° C.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-0f4377e8640246c0b12476d1fd85b086
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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