Tetrabutylammonium Fluoride → 2-Cyano-4-(3-furyl)-7-mercaptonaphthalene

HRID 741836Notes

Reaction equation

HRID 741836 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:24]=[CH:23][O:22][CH:21]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([S:13]CC[Si](C)(C)C)=[CH:8][CH:7]=2)#[N:2].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>CN(C=O)C.C1COCC1.Cl>[C:1]([C:3]1[CH:4]=[C:5]([C:20]2[CH:24]=[CH:23][O:22][CH:21]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([SH:13])=[CH:8][CH:7]=2)#[N:2]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 194269713-Cyano-1-(furan-3-yl)-6-[2-trimethylsilylethylthio]naphthalene

Product 1

HCID 233702312-Cyano-4-(3-furyl)-7-mercaptonaphthaleneYield 82.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Step 1 (1.8 g) was dissolved in DMF (40 mL) and there was added n-Bu4NF (1M) in THF (15 mL). The resulting mixture was stirred at r.t. for 1.5 h, diluted with 1N aqueous HCl (40 mL) then H2O (300 mL) and filtered to afford the title thiol (1.06 g) as a light orange solid m.p.: 144°-146° C.

Workup

  1. filtrationH2O (300 mL) and filtered

Sources & evidence

ORD record
ord-a737a7ab637e4d72a3fcf62e015646b0
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

Loading…