Tetrabutylammonium Fluoride → HCID 18665565, compound

HRID 2395368Notes

Reaction equation

HRID 2395368 reaction equation
[Si](O[CH2:9][C@H:10]([NH:17][C:18](=[S:26])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[I:25][C:21]1[CH:20]=[C:19]([C:18]2[S:26][CH2:9][C@@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:17]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54141665HCID 54141665, compound

Product 1

HCID 18665565HCID 18665565, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(1-tert-butyldimethylsilyloxy-2(R)-phenylethan-2-yl)-3-iodobenzthiamide (8.1 g, 16 mmol) in THF (70 ml) was added dropwise tetrabutyl-ammonium fluoride (1M in THF, 21 ml). The reaction mixture was stirred at room temperature for 4 hours, solvent removed by evaporation and the resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:7) to afford 4,5-dihydro-2-(3-iodophenyl)-4(R)-phenylthiazole (2.46 g, 41%).

Workup

  1. customsolvent removed by evaporation
  2. customthe resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate/n-hexane (=1:7)

Sources & evidence

ORD record
ord-3fe396e0131e431d8575c39e46e8c085
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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