Potassium Fluoride → 5-(4-Benzyloxyphenyl)-6-methyl-1-indanone

HRID 1352201Notes

Reaction equation

HRID 1352201 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[C:12](=[O:17])[CH2:11][CH2:10]2)(=O)=O.[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[F-].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[CH3:16])[C:12](=[O:17])[CH2:11][CH2:10]3)=[CH:30][CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 522689Potassium FluorideHCID 27343144-Benzyloxy-phenylboronic acidHCID 211000385-(Trifluoromethanesulfonyloxy)-6-methyl-1-indanone

Product 1

HCID 211000315-(4-Benzyloxyphenyl)-6-methyl-1-indanoneYield 119.4%

Reagents, catalysts & solvents 3

HCID 75806TricyclohexylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(trifluoromethanesulfonyloxy)-6-methyl-1-indanone 0.15 g, 0.51 mmol, from Step A), 4-benzyloxyphenyl boronic acid (0.17 g, 0.77 mmol), palladium acetate (5.7 mg, 0.025 mmol), tricyclohexylphosphine (8.6 mg, 0.030 mmol) and potassium fluoride (0.098 g, 1.68 mmol) in tetrahydrofuran (2.5 mL) was stirred at rt. After 5 min, the reaction was loaded onto silica gel and the product eluted with 25% ethyl acetate/hexanes to give a yellow solid (0.20 g): ESI-MS 329.1 (M+H).

Workup

  1. washthe product eluted with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c9683a6b9efb47d3b02a102f16de8109
Source dataset
uspto-grants-2007_05
Patent number
US07220734B2

Reaction notes

Loading…