Diethyl Ether → {7-[4-(4-Chloro-phenyl)-4-oxo-butylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester

HRID 1296037Notes

Reaction equation

HRID 1296037 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([SH:15])=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2.Cl[CH2:18][CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+].CCOCC>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:12]([S:15][CH2:18][CH2:19][CH2:20][C:21]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[O:22])=[C:11]2[C:7]=1[CH2:8][CH2:9][CH2:10]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 27237814,4'-DichlorobutyrophenoneHCID 20770872(7-Mercapto-indan-4-yloxy)-acetic Acid Methyl Ester

Product 1

HCID 20770865{7-[4-(4-Chloro-phenyl)-4-oxo-butylsulfanyl]-indan-4-yloxy}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 1D (300 mg, 1.26 mmol), 4-chloro-1-(4-chloro-phenyl)-butan-1-one (327 mg, 1.51 mmol), and cesium carbonate (616 mg, 1.89 mmol) in 10 ml anhydrous acetonitrile were stirred at ambient temperature for 72 hours. The reaction was then run through 0.5 g SiO2 eluting with Et2O. The eluant was collected and concentrated to give the title compound, pure enough for subsequent use. MS m/z 419 (M+1).

Workup

  1. customThe eluant was collected
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-156d121ca3e34413933bf59835849e0b
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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