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

HRID 1901128Notes

Reaction equation

HRID 1901128 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>[O:19]1[CH:20]=[CH:21][C:17]([C:10]2[C:9]3[C:14](=[CH:15][C:6]([SH:5])=[CH:7][CH:8]=3)[O:13][C:12](=[O:16])[CH:11]=2)=[CH:18]1

Participants

7

Reactant 3

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

Product 1

HCID 233701944-(3-Furyl)-7-mercaptocoumarin

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 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 (50 mL) and filtered to afford the title compound as a tan solid.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-4c99c5efa2be44f4b1ff6a4c589ac0db
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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