1-{4-[(6-Bromohexyl)oxy]-1-butyn-1-yl}-3-(cyclopentylsulfonyl)benzene → 1-{4-[(6-Bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene

HRID 2118345Notes

Reaction equation

HRID 2118345 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]#[C:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=[O:21])=[O:20])[CH:14]=1>[Pd].CCOC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)(=[O:21])=[O:20])[CH:14]=1

Participants

4

Reactant 1

HCID 691198231-{4-[(6-Bromohexyl)oxy]-1-butyn-1-yl}-3-(cyclopentylsulfonyl)benzene

Product 1

HCID 691198271-{4-[(6-Bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an evacuated flask, containing palladium on carbon [50% water by weight] (43 mg) was added a solution of 1{4-[(6-bromohexyl)oxy]-1-butyn-1-yl}-3-(cyclopentylsulfonyl) benzene (304 mg) in EtOAc (10 ml). The mixture was hydrogenated for 19 h. The catalyst was filtered off and the filtrate was concentrated in vacuo to afford title compound. LCMS RT=3.92 min

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-79ec8e1c85984fe5a2e3834e64d3a175
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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