Sodium Carbonate → Methyl 4-cyclopropyl-2-isopropoxybenzoate

HRID 531025ノート

反応式

HRID 531025 の反応式
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.I[C:43]1[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[C:45]([O:53][CH:54]([CH3:56])[CH3:55])[CH:44]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:1]1([C:43]2[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[C:45]([O:53][CH:54]([CH3:56])[CH3:55])[CH:44]=2)[CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90422834Methyl 4-iodo-2-isopropoxybenzoate

生成物 1

HCID 90423653Methyl 4-cyclopropyl-2-isopropoxybenzoate収率 93.7%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Cyclopropylboronic acid (3.19 g), a 2 M aqueous sodium carbonate solution (37 mL), tris(dibenzylideneacetone)dipalladium(0) (1.59 g), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.52 g) were added at room temperature to a toluene (100 mL) solution of methyl 4-iodo-2-isopropoxybenzoate (7.92 g), and the mixture was stirred at 100° C. for 15 hours in an argon atmosphere. Water was added to the reaction mixture at room temperature. The mixture was filtered through celite, and then, the filtrate was subjected to extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (5.43 g).

後処理

  1. filtrationThe mixture was filtered through celite
  2. extractionthe filtrate was subjected to extraction with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated saline in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-5761e36d9b4e48df8815d2dd3525db3d
出典データセット
uspto-grants-2016_05
特許番号
US09353108B2

反応ノート

読み込み中…