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

HRID 2076637Notes

Reaction equation

HRID 2076637 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 882672-Methylphenethyl alcoholSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-343098afb05a4a24a3ec0d5959fe4bcb
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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