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

HRID 2103618Notes

Reaction equation

HRID 2103618 reaction equation
[CH:1]1(/[CH:6]=[C:7](/B2OC(C)(C)C(C)(C)O2)\[CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:20]1[CH:21]=[C:22]([S:25]([CH3:28])(=[O:27])=[O:26])[S:23][CH:24]=1.[F-].[Cs+]>[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:1]1(/[CH:6]=[C:7](\[C:20]2[CH:21]=[C:22]([S:25]([CH3:28])(=[O:27])=[O:26])[S:23][CH:24]=2)/[CH2:8][OH:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 202222934-Bromo-2-methylsulfonyl-thiopheneHCID 67487170(Z)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 67484562(E)-3-Cyclopentyl-2-(5-methanesulfonyl-thiophen-3-yl)-prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

According to method 20b was used (Z)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (252 mg, 1.0 mmol), 4-Bromo-2-methanesulfonyl-thiophene (241 mg, 1.0 mmol), caesium fluoride ( 304 mg, 2.0 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (58 mg, 0.05 mmol) to give 100 mg purified product. MS (m/e): 309.0 (M+Na).

Workup

  1. customto give 100 mg
  2. custompurified product

Sources & evidence

ORD record
ord-c687ecaedd8540b6a5123b170f5261ce
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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