Cesium fluoride → (Z)-3-Cyclopentyl-2-(5-methanesulfonyl-thiophen-2-yl)-prop-2-en-1-ol

HRID 2103613Notes

Reaction equation

HRID 2103613 reaction equation
Br[C:2]1[S:3][C:4]([S:7]([CH3:10])(=[O:9])=[O:8])=[CH:5][CH:6]=1.[F-].[Cs+].[CH:13]1([CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]1(/[CH:18]=[C:19](\[C:2]2[S:3][C:4]([S:7]([CH3:10])(=[O:9])=[O:8])=[CH:5][CH:6]=2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 173902812-Bromo-5-methanesulfonylthiopheneHCID 670847173-Cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 69055089(Z)-3-Cyclopentyl-2-(5-methanesulfonyl-thiophen-2-yl)-prop-2-en-1-olYield 56.1%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

According to method 17a was used 2-bromo-5-methanesulfonyl-thiophene (593 mg, 2.46 mmol), caesium fluoride ( 747 mg, 4.92 mmol), tetrakis-(triphenylphosphin)-palladium(0) (142 mg, 0.123 mmol) and 3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (620 g, 2.46 mmol) to give 395 mg of purified compound. MS (m/e): 309.0 (M+Na).

Sources & evidence

ORD record
ord-1614bab49cd64e9aa521ac7e802bbdcd
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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