2-Cyclopenten-1-one → ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate

HRID 1627070Notes

Reaction equation

HRID 1627070 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:8]=1)[CH3:2].[C:27]1(=[O:32])[CH2:31][CH2:30][CH:29]=[CH:28]1>F[B-](F)(F)F>[O:32]=[C:27]1[CH2:31][CH2:30][C@@H:29]([C:9]2[CH:8]=[C:7]([CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=2)[O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:26])[CH2:28]1

Participants

4

Reactant 2

HCID 135882-Cyclopenten-1-oneHCID 68790116[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-phenoxy]-acetic acid ethyl ester

Product 1

HCID 49834558ethyl 2-[3-[(1R)-3-oxocyclopentyl]-5-(trifluoromethyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 26255TetrafluoroborateCatalyst

Procedure

The title compound was prepared from [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-phenoxy]-acetic acid ethyl ester and 2-cyclopenten-1-one with Rh(R-BINAP)(nbd)]BF4 as catalyst in a manner similar to the one described for Preparation 6.

Workup

  1. customdescribed for Preparation 6

Sources & evidence

ORD record
ord-e9e0101b740944f5afafb60d79a76b59
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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