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Water → Ethyl[5-(4-hydroxyphenyl)-2-thienyl]acetate

HRID 2076637
ノート
印刷プレビュー

反応式

HRID 2076637 の反応式
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)O1.Br[C:24]1[S:28][C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=1.O>C1(C)C(CCO)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C:24]2[S:28][C:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=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 962WaterHCID 10340Sodium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 14792376Ethyl 2-(5-bromothiophen-2-yl)acetate

生成物 1

HCID 86088129Ethyl[5-(4-hydroxyphenyl)-2-thienyl]acetate収率 77%

試薬・触媒・溶媒 3

HCID 80271
Tri-o-tolylphosphine
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 882672-Methylphenethyl alcohol溶媒

反応条件

温度
80 °C

実験手順

After tris(dibenzylideneacetone)dipalladium (0) (110 mg, 0.12 mmol), tri-o-tolylphosphine (61 mg, 0.2 mmol) and 2N aqueous sodium carbonate solution (4 ml) were added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.8 g, 3.65 mmol) and ethyl (5-bromo-2-thienyl)acetate (1.00 g, 4.01 mmol) which was synthesized according to the method described in literature (Jackson, P. M. et al., J. Chem. Soc. Perkin Trans. 1, 1990, vol. 11, pp. 2909-2918) in a mixture of toluene-ethanol (5:1, 24 ml), the mixture was stirred at 80° C. for 3 hours. After water was poured into the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1) to give ethyl [5-(4-hydroxyphenyl)-2-thienyl]acetate (0.73 g, yield: 77%).

後処理

  1. customwas synthesized
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-343098afb05a4a24a3ec0d5959fe4bcb
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07923573B2

反応ノート

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