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Sodium Carbonate → Methyl 4-cyclopropyl-2-ethoxybenzoate

HRID 531051
ノート
印刷プレビュー

反応式

HRID 531051 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.[CH2:42]([O:44][C:45]1[CH:54]=[C:53](I)[CH:52]=[CH:51][C:46]=1[C:47]([O:49][CH3:50])=[O:48])[CH3:43]>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:53]2[CH:52]=[CH:51][C:46]([C:47]([O:49][CH3:50])=[O:48])=[C:45]([O:44][CH2:42][CH3:43])[CH:54]=2)[CH2:3][CH2:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66635397Methyl 2-ethoxy-4-iodobenzoate

生成物 1

HCID 90423210Methyl 4-cyclopropyl-2-ethoxybenzoate収率 100.1%

試薬・触媒・溶媒 3

HCID 9811564
Bis(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 (1.90 g), a 2 M aqueous sodium carbonate solution (22 mL), tris(dibenzylideneacetone)dipalladium(0) (944 mg), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (907 mg) were added at room temperature to a toluene (80 mL) solution of methyl 2-ethoxy-4-iodobenzoate (4.51 g), and the mixture was stirred at 100° C. for 18 hours in an argon atmosphere. Water was added to the reaction mixture at room temperature, and the mixture was filtered through celite. 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 (3.25 g).

後処理

  1. filtrationthe mixture was filtered through celite
  2. extractionThen, the 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-de80f0c04aa545a5a38e8697fb336ec8
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09353108B2

反応ノート

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