Water → 6-But-2-ynyloxy-benzofuran-2-carboxlic acid ethyl ester

HRID 1171205Notes

Reaction equation

HRID 1171205 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]#[C:21][CH3:22].O>O1CCCC1.CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][CH2:19][C:20]#[C:21][CH3:22])[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 66786469Ethyl 6-hydroxybenzofuran-2-carboxylate

Product 1

HCID 576082296-But-2-ynyloxy-benzofuran-2-carboxlic acid ethyl esterYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 6-hydroxy-benzofuran-2-carboxylic acid ethyl ester (250 mg, 1.21 mmol) in tetrahydrofuran (5 mL) and N,N-dimethylformamide (5 mL) were added sodium hydride (58 mg, 2.42 mmol) and 1-bromo-2-butyne (127 μL) at room temperature, which was stirred at room temperature for 1 hour. Water was added to the reaction solution followed by extraction with ethyl acetate. The organic layer was washed with water and sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (254 mg, 81%) as a white solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3745deb4c8f3495080f95eab01c48d8b
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

Loading…