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Sodium Carbonate → Methyl 4,5-dicyclopropyl-2-isopropoxybenzoate

HRID 2272475
ノート
印刷プレビュー

反応式

HRID 2272475 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.Br[C:43]1[C:44]([CH:57]2[CH2:59][CH2:58]2)=[CH:45][C:46]([O:53][CH:54]([CH3:56])[CH3:55])=[C:47]([CH:52]=1)[C:48]([O:50][CH3:51])=[O:49]>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:57]1([C:44]2[C:43]([CH:1]3[CH2:3][CH2:2]3)=[CH:52][C:47]([C:48]([O:50][CH3:51])=[O:49])=[C:46]([O:53][CH:54]([CH3:56])[CH3:55])[CH:45]=2)[CH2:59][CH2:58]1
参加物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 90423660Methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate

生成物 1

HCID 90423073Methyl 4,5-dicyclopropyl-2-isopropoxybenzoate収率 97.8%

試薬・触媒・溶媒 3

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

実験手順

Cyclopropylboronic acid (2.83 g), a 2 M aqueous sodium carbonate solution (33 mL), tris(dibenzylideneacetone)dipalladium(0) (1.41 g), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.36 g) were added at room temperature to a toluene (100 mL) solution of methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate (6.89 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 (5.90 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-1800e9ef298c4d96b549eace14b10749
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120777B2

反応ノート

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