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

HRID 2076637
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HRID 2076637 반응식
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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 80271
Tri-o-tolylphosphine
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 882672-Methylphenethyl alcohol용매

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온도
80 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-343098afb05a4a24a3ec0d5959fe4bcb
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07923573B2

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