Cesium carbonate → HCID 11725342、化合物

HRID 2245784ノート

反応式

HRID 2245784 の反応式
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 742994-Chlorophenylboronic acidHCID 100871716-(4-Bromo-phenylsulfanyl)-hexanoic acid methyl ester

生成物 1

HCID 11725342HCID 11725342、化合物収率 84.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a degassed solution of 6-(4-bromo-phenylsulfanyl)-hexanoic acid methyl ester (500 mg, 1.58 mmol) in ethylene glycol dimethyl ether (20 mL) was added 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (131 mg, 0.16 mmol). The resulting mixture was stirred for 5 min at room temperature under an argon atmosphere. 4-Chlorophenylboronic acid (494 mg, 3.16 mmol) was added. A solution of cesium carbonate (1.8 g, 5.54 mmol) in water (3 mL) was added. The mixture was stirred at reflux for 1 hour, allowed to cool down to room temperature and concentrated under reduced pressure. The residue was taken up in ethyl acetate (75 mL). This solution was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL), distilled water (2×50 mL) and brine (2×50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (5:95 to 10:90 diethyl ether:40-60° C. petroleum ether) to give a solid that was recrystallised from diethyl ether/40-60° C. petroleum ether to give the title compound (465 mg, 84%) as a solid, mp 87-88° C.

後処理

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 1 hour
  3. temperatureto cool down to room temperature
  4. concentrationconcentrated under reduced pressure
  5. washThis solution was washed with saturated aqueous sodium hydrogen carbonate (2×50 mL)
  6. distillationdistilled water (2×50 mL) and brine (2×50 mL)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (5:95 to 10:90 diethyl ether:40-60° C. petroleum ether)
  11. customto give a solid
  12. customthat was recrystallised from diethyl ether/40-60° C. petroleum ether

出典と根拠

ORDレコード
ord-0c4381eabce6442db34307f729960578
出典データセット
uspto-grants-2010_03
特許番号
US07683185B2

反応ノート

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